U.S. patent number 11,011,711 [Application Number 15/424,390] was granted by the patent office on 2021-05-18 for organometallic compound, organic light-emitting device including the organometallic compound, and diagnosis composition incluidng the organometallic compound.
This patent grant is currently assigned to SAMSUNG ELECTRONICS CO., LTD.. The grantee listed for this patent is SAMSUNG ELECTRONICS CO., LTD.. Invention is credited to Hyeonho Choi, Soyeon Kim, Hyun Koo, Yoonhyun Kwak, Ohyun Kwon, Youngjae Park.
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United States Patent |
11,011,711 |
Kim , et al. |
May 18, 2021 |
Organometallic compound, organic light-emitting device including
the organometallic compound, and diagnosis composition incluidng
the organometallic compound
Abstract
An organometallic compound represented by Formula 1:
##STR00001## wherein in Formula 1, groups and variables are the
same as described in the specification.
Inventors: |
Kim; Soyeon (Seoul,
KR), Kwak; Yoonhyun (Seoul, KR), Kwon;
Ohyun (Seoul, KR), Choi; Hyeonho (Seoul,
KR), Koo; Hyun (Seoul, KR), Park;
Youngjae (Seoul, KR) |
Applicant: |
Name |
City |
State |
Country |
Type |
SAMSUNG ELECTRONICS CO., LTD. |
Suwon-si |
N/A |
KR |
|
|
Assignee: |
SAMSUNG ELECTRONICS CO., LTD.
(Gyeonggi-Do, KR)
|
Family
ID: |
58192062 |
Appl.
No.: |
15/424,390 |
Filed: |
February 3, 2017 |
Prior Publication Data
|
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|
|
Document
Identifier |
Publication Date |
|
US 20170237023 A1 |
Aug 17, 2017 |
|
Foreign Application Priority Data
|
|
|
|
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Feb 11, 2016 [KR] |
|
|
10-2016-0015678 |
|
Current U.S.
Class: |
1/1 |
Current CPC
Class: |
C09K
11/06 (20130101); H01L 51/0087 (20130101); H05B
33/14 (20130101); C09K 11/00 (20130101); A61K
49/0015 (20130101); C09K 11/025 (20130101); C07F
15/0086 (20130101); H01L 51/0072 (20130101); G01N
33/52 (20130101); C09K 2211/1088 (20130101); H01L
51/5012 (20130101); C09K 2211/1029 (20130101); C09K
2211/1092 (20130101); C09K 2211/1007 (20130101); C09K
2211/1011 (20130101); C09K 2211/1022 (20130101); C09K
2211/1014 (20130101); C09K 2211/185 (20130101); H01L
51/5016 (20130101) |
Current International
Class: |
H01L
51/00 (20060101); G01N 33/52 (20060101); A61K
49/00 (20060101); C07F 15/00 (20060101); C09K
11/02 (20060101); C09K 11/06 (20060101); H05B
33/14 (20060101); C09K 11/00 (20060101); H01L
51/50 (20060101) |
References Cited
[Referenced By]
U.S. Patent Documents
Foreign Patent Documents
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|
|
2891659 |
|
Jul 2015 |
|
EP |
|
10-2016-0037007 |
|
Apr 2016 |
|
KR |
|
2005058149 |
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Jun 2005 |
|
WO |
|
Other References
Extended Search Report dated Jul. 18, 2017, issued by the European
Patent Office for EP Patent Application No. 17155485.0-1451. cited
by applicant .
English Translation of Office Action issued by the Chinese Patent
Office dated Jun. 17, 2020 in the examination of the Chinese Patent
Application No. 201710066097.X, which corresponds to the U.S.
Application above. cited by applicant .
Office Action issued by the Chinese Patent Office dated Jun. 17,
2020 in the examination of the Chinese Patent Application No.
201710066097.X, which corresponds to the U.S. Application above.
cited by applicant.
|
Primary Examiner: Yang; Jay
Attorney, Agent or Firm: Cantor Colburn LLP
Claims
What is claimed is:
1. An organometallic compound represented by Formula 1:
##STR00095## wherein in Formula 1, X.sub.1 is O or S, X.sub.2 is C,
and X.sub.3 and X.sub.4 are each N, a bond between Pt and X.sub.1
and a bond between Pt and X.sub.2 are each a covalent bond, and a
bond between Pt and X.sub.3 and a bond between Pt and X.sub.4 are
each a coordinate bond, Y.sub.1 and Y.sub.3 to Y.sub.8 are each
independently C or N, Y.sub.2 and Y.sub.9 are each independently C,
N, O, or S, Y.sub.1 and Y.sub.2 are connected to each other via a
single bond or a double bond, Y.sub.1 and Y.sub.3 are connected to
each other via a single bond or a double bond, X.sub.2 and Y.sub.4
are connected to each other via a single bond or a double bond,
X.sub.2 and Y.sub.5 are connected to each other via a single bond
or a double bond, X.sub.3 and Y.sub.6 are connected to each other
via a single bond or a double bond, X.sub.3 and Y.sub.7 are
connected to each other via a single bond or a double bond, X.sub.4
and Y.sub.8 are connected to each other via a single bond or a
double bond, and X.sub.4 and Y.sub.9 are connected to each other
via a single bond or a double bond, CY.sub.1 to CY.sub.4 are each
independently selected from a C.sub.5-C.sub.30 carbocyclic group
and a C.sub.1-C.sub.30 heterocyclic group, T.sub.1 is a single
bond, T.sub.2 is selected from a single bond, *--O--*', *--S--*',
*--C(R.sub.5)(R.sub.6)--*', *--C(R.sub.5).dbd.C(R.sub.6)--*',
*--C(.dbd.O)--*', *--C(.dbd.S)--*', *--C.ident.C--*',
*--N(R.sub.5)--*', *--Si(R.sub.5)(R.sub.6)--*', and
*--P(R.sub.5)(R.sub.6)--*', wherein * and *' in each of the
foregoing groups independently indicate a binding site to a
neighboring atom, T.sub.3 is a group selected from
*--C(R.sub.7)(R.sub.8)--*', *--Si(R.sub.7)(R.sub.8)--*', and
*--P(R.sub.7)(R.sub.8)--*', wherein * and *' in each of the
foregoing groups independently indicate a binding site to a
neighboring atom, b1 to b3 are 1, R.sub.5 and R.sub.6 are
optionally connected to each other via a first linking group to
form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic
group or a substituted or unsubstituted C.sub.1-C.sub.30
heterocyclic group, R.sub.1 to R.sub.6 and R.sub.9 to R.sub.10 are
each independently selected from hydrogen, deuterium, --F, --Cl,
--Br, --I, --SF.sub.5, a hydroxy group, a cyano group, a nitro
group, a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group,
a substituted or unsubstituted C.sub.2-C.sub.60 alkenyl group, a
substituted or unsubstituted C.sub.2-C.sub.60 alkynyl group, a
substituted or unsubstituted C.sub.1-C.sub.60 alkoxy group, a
substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a
substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl
group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl
group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkenyl group, a substituted or unsubstituted
C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted
C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted
C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted
C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted
monovalent non-aromatic condensed polycyclic group, a substituted
or unsubstituted monovalent non-aromatic condensed heteropolycyclic
group, --N(Q.sub.1)(Q.sub.2), --Si(Q.sub.3)(Q.sub.4)(Q.sub.5),
--B(Q.sub.6)(Q.sub.7), and --P(.dbd.O)(Q.sub.8)(Q.sub.9), a1 to a4
are each independently 0, 1, 2, 3, 4, or 5, two groups selected
from groups R.sub.1 in the number of a1 are optionally connected to
each other to form a substituted or unsubstituted C.sub.5-C.sub.30
carbocyclic group or a substituted or unsubstituted
C.sub.1-C.sub.30 heterocyclic group, two groups selected from
groups R.sub.2 in the number of a2 are optionally connected to each
other to form a substituted or unsubstituted C.sub.5-C.sub.30
carbocyclic group or a substituted or unsubstituted
C.sub.1-C.sub.30 heterocyclic group, two group selected from groups
R.sub.3 in the number of a3 are optionally connected to each other
to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic
group or a substituted or unsubstituted C.sub.1-C.sub.30
heterocyclic group, two groups selected from groups R.sub.4 in the
number of a4 are optionally connected to each other to form a
substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or
a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group,
two or more neighboring groups selected from R.sub.1 to R.sub.4 are
optionally connected to each other to form a substituted or
unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted
or unsubstituted C.sub.1-C.sub.30 heterocyclic group, R.sub.7 and
R.sub.8 are each independently selected from a substituted or
unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or
unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or
unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or
unsubstituted C.sub.1-C.sub.60 alkoxy group, a substituted or
unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or
unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a
substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a
substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl
group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group,
a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a
substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a
substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a
substituted or unsubstituted monovalent non-aromatic condensed
polycyclic group, and a substituted or unsubstituted monovalent
non-aromatic condensed heteropolycyclic group, R.sub.7 and R.sub.8
are connected to each other via a second linking group, the second
linking group is selected from a single bond, *--O--*', *--S--*',
*--C(R.sub.10)(R.sub.10)--*', *--C(R.sub.10).dbd.C(R.sub.10)--*',
*--C(.dbd.O)--*', *--C(.dbd.S)--*', *--N(R.sub.10)--*',
*--Si(R.sub.10)(R.sub.10)--*', and *--P(R.sub.10)(R.sub.10)--*',
wherein * and *' in each of the foregoing groups independently
indicate a binding site to a neighboring atom, at least one
substituent selected from a substituent(s) of the substituted
C.sub.5-C.sub.30 carbocyclic group, the substituted
C.sub.1-C.sub.30 heterocyclic group, the substituted
C.sub.1-C.sub.60 alkyl group, the substituted C.sub.2-C.sub.60
alkenyl group, the substituted C.sub.2-C.sub.60 alkynyl group, the
substituted C.sub.1-C.sub.60 alkoxy group, the substituted
C.sub.3-C.sub.10 cycloalkyl group, the substituted C.sub.1-C.sub.10
heterocycloalkyl group, the substituted C.sub.3-C.sub.10
cycloalkenyl group, the substituted C.sub.1-C.sub.10
heterocycloalkenyl group, the substituted C.sub.6-C.sub.60 aryl
group, the substituted C.sub.6-C.sub.60 aryloxy group, the
substituted C.sub.6-C.sub.60 arylthio group, the substituted
C.sub.1-C.sub.60 heteroaryl group, the substituted monovalent
non-aromatic condensed polycyclic group, and the substituted
monovalent non-aromatic condensed heteropolycyclic group is
selected from: deuterium, --F, --Cl, --Br, --I, --CD.sub.3,
--CD.sub.2H, --CDH.sub.2, --CF.sub.3, --CF.sub.2H, --CFH.sub.2, a
hydroxy group, a cyano group, a nitro group, a C.sub.1-C.sub.60
alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60
alkynyl group, and a C.sub.1-C.sub.60 alkoxy group; a
C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a
C.sub.2-C.sub.60 alkynyl group, and a C.sub.1-C.sub.60 alkoxy
group, each substituted with at least one selected from deuterium,
--F, --Cl, --Br, --I, --CD.sub.3, --CD.sub.2H, --CDH.sub.2,
--CF.sub.3, --CF.sub.2H, --CFH.sub.2, a hydroxy group, a cyano
group, a nitro group, a C.sub.3-C.sub.10 cycloalkyl group, a
C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10
cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a
C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a
C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl
group, a monovalent non-aromatic condensed polycyclic group, a
monovalent non-aromatic condensed heteropolycyclic group,
--N(Q.sub.11)(Q.sub.12), --Si(Q.sub.13)(Q.sub.14(Q.sub.15),
--B(Q.sub.16)(Q.sub.17), and --P(.dbd.O)(Q.sub.18)(Q.sub.19); a
C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60
arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, and a monovalent
non-aromatic condensed heteropolycyclic group; a C.sub.3-C.sub.10
cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a
C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10
heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a
C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group,
a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic
condensed polycyclic group, and a monovalent non-aromatic condensed
heteropolycyclic group, each substituted with at least one selected
from deuterium, --F, --Cl, --Br, --I, --CD.sub.3, --CD.sub.2H,
--CDH.sub.2, --CF.sub.3, --CF.sub.2H, --CFH.sub.2, a hydroxy group,
a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group, a
C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a
C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group,
a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10
cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a
C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a
C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl
group, a monovalent non-aromatic condensed polycyclic group, a
monovalent non-aromatic condensed heteropolycyclic group,
--N(Q.sub.21)(Q.sub.22), --Si(Q.sub.23)(Q.sub.24)(Q.sub.25),
--B(Q.sub.26)(Q.sub.27), and --P(.dbd.O)(Q.sub.28)(Q.sub.29); and
--N(Q.sub.31)(Q.sub.32), --Si(Q.sub.33)(Q.sub.34)(Q.sub.35),
--B(Q.sub.36)(Q.sub.37), and --P(.dbd.O)(Q.sub.38)(Q.sub.39), and
wherein Q.sub.1 to Q.sub.9, Q.sub.11 to Q.sub.19, Q.sub.21 to
Q.sub.29, and Q.sub.31 to Q.sub.39 are each independently selected
from hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group, a
C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a
C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group,
a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10
cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a
C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryl group
substituted with at least one selected from a C.sub.1-C.sub.60
alkyl group and a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60
aryloxy group, a C.sub.6-C.sub.60 arylthio group, a
C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic
condensed polycyclic group, and a monovalent non-aromatic condensed
heteropolycyclic group.
2. The organometallic compound of claim 1, wherein R.sub.1 to
R.sub.6 are each independently selected from: hydrogen, deuterium,
--F, --Cl, --Br, --I, a hydroxy group, a cyano group, a nitro
group, --SF.sub.5, a C.sub.1-C.sub.20 alkyl group, and a
C.sub.1-C.sub.20 alkoxy group; a C.sub.1-C.sub.20 alkyl group and a
C.sub.1-C.sub.20 alkoxy group, each substituted with at least one
selected from deuterium, --F, --Cl, --Br, --I, --CD.sub.3,
--CD.sub.2H, --CDH.sub.2, --CF.sub.3, --CF.sub.2H, --CFH.sub.2, a
hydroxy group, a cyano group, a nitro group, a C.sub.1-C.sub.10
alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl
group, a cyclooctyl group, an adamantanyl group, a norbornanyl
group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl
group, a cycloheptenyl group, a phenyl group, a naphthyl group, a
pyridinyl group, and a pyrimidinyl group; a cyclopentyl group, a
cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an
adamantanyl group, a norbornanyl group, a norbornenyl group, a
cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a
phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a
thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl
group, a thiazolyl group, an isothiazolyl group, an oxazolyl group,
an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a
pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an
indolyl group, an indazolyl group, a purinyl group, a quinolinyl
group, an isoquinolinyl group, a benzoquinolinyl group, a
quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a
carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group,
a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl
group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl
group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group,
a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, an
imidazopyridinyl group, and an imidazopyrimidinyl group; a
cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a
cyclooctyl group, an adamantanyl group, a norbornanyl group, a
norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a
cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl
group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl
group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a
pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl
group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group,
an oxazolyl group, an isoxazolyl group, a pyridinyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an
isoindolyl group, an indolyl group, an indazolyl group, a purinyl
group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group,
a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a
benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl
group, an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a
dibenzothiophenyl group, a benzocarbazolyl group, a
dibenzocarbazolyl group, an imidazopyridinyl group, and an
imidazopyrimidinyl group, each substituted with at least one
selected from deuterium, --F, --Cl, --Br, --I, --CD.sub.3,
--CD.sub.2H, --CDH.sub.2, --CF.sub.3, --CF.sub.2H, --CFH.sub.2, a
hydroxy group, a cyano group, a nitro group, a C.sub.1-C.sub.20
alkyl group, a C.sub.1-C.sub.20 alkoxy group, a cyclopentyl group,
a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an
adamantanyl group, a norbornanyl group, a norbornenyl group, a
cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a
phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a
thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl
group, a thiazolyl group, an isothiazolyl group, an oxazolyl group,
an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a
pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an
indolyl group, an indazolyl group, a purinyl group, a quinolinyl
group, an isoquinolinyl group, a benzoquinolinyl group, a
quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a
carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group,
a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl
group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl
group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group,
a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, an
imidazopyridinyl group, and an imidazopyrimidinyl group; and
--N(Q.sub.1)(Q.sub.2), --Si(Q.sub.3)(Q.sub.4)(Q.sub.5),
--B(Q.sub.6)(Q.sub.7), and --P(.dbd.O)(Q.sub.8)(Q.sub.9), wherein
Q.sub.1 to Q.sub.9 are each independently selected from:
--CH.sub.3, --CD.sub.3, --CD.sub.2H, --CDH.sub.2,
--CH.sub.2CH.sub.3, --CH.sub.2CD.sub.3, --CH.sub.2CD.sub.2H,
--CH.sub.2CDH.sub.2, --CHDCH.sub.3, --CHDCD.sub.2H, --CHDCDH.sub.2,
--CHDCD.sub.3, --CD.sub.2CD.sub.3, --CD.sub.2CD.sub.2H, and
--CD.sub.2CDH.sub.2; an n-propyl group, an iso-propyl group, an
n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl
group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group,
a tert-pentyl group, a phenyl group, and a naphthyl group; and an
n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl
group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an
iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl
group, and a naphthyl group, each substituted with at least one
selected from deuterium, a C.sub.1-C.sub.10 alkyl group, and a
phenyl group.
3. The organometallic compound of claim 1, wherein R.sub.1 to
R.sub.6 are each independently selected from: hydrogen, deuterium,
--F, a cyano group, a nitro group, --SF.sub.5, a methyl group, an
ethyl group, an n-propyl group, an iso-propyl group, an n-butyl
group, an iso-butyl group, a sec-butyl group, a tert-butyl group,
an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a
tert-pentyl group, an n-hexyl group, an iso-hexyl group, a
sec-hexyl group, a tert-hexyl group, an n-heptyl group, an
iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an
n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl
group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a
tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl
group, a tert-decyl group, a methoxy group, an ethoxy group, a
propoxy group, a butoxy group, a pentoxy group, a cyclopentyl
group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group,
an adamantanyl group, a norbornanyl group, a norbornenyl group, a
cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a
phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl
group, a carbazolyl group, a dibenzofuranyl group, and a
dibenzothiophenyl group; a methyl group, an ethyl group, an
n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl
group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an
iso-pentyl group, a sec-pentyl group, a tert-pentyl group, an
n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl
group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group,
a tert-heptyl group, an n-octyl group, an iso-octyl group, a
sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl
group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an
iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy
group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy
group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl
group, a cyclooctyl group, an adamantanyl group, a norbornanyl
group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl
group, a cycloheptenyl group, a phenyl group, a naphthyl group, a
pyridinyl group, a pyrimidinyl group, a carbazolyl group, a
dibenzofuranyl group, and a dibenzothiophenyl group, each
substituted with at least one selected from deuterium, --F,
--CD.sub.3, --CD.sub.2H, --CDH.sub.2, --CF.sub.3, --CF.sub.2H,
--CFH.sub.2, a cyano group, a nitro group, a C.sub.1-C.sub.10 alkyl
group, a C.sub.1-C.sub.10 alkoxy group, a cyclopentyl group, a
cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an
adamantanyl group, a norbornanyl group, a norbornenyl group, a
cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a
phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl
group, a carbazolyl group, a dibenzofuranyl group, and a
dibenzothiophenyl group; and --N(Q.sub.1)(Q.sub.2),
--Si(Q.sub.3)(Q.sub.4)(Q.sub.5), --B(Q.sub.6)(Q.sub.7), and
--P(.dbd.O)(Q.sub.8)(Q.sub.9), wherein Q.sub.1 to Q.sub.9 are each
independently selected from: --CH.sub.3, --CD.sub.3, --CD.sub.2H,
--CDH.sub.2, --CH.sub.2CH.sub.3, --CH.sub.2CD.sub.3,
--CH.sub.2CD.sub.2H, --CH.sub.2CDH.sub.2, --CHDCH.sub.3,
--CHDCD.sub.2H, --CHDCDH.sub.2, --CHDCD.sub.3, --CD.sub.2CD.sub.3,
--CD.sub.2CD.sub.2H, and --CD.sub.2CDH.sub.2; an n-propyl group, an
iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl
group, a tert-butyl group, an n-pentyl group, an iso-pentyl group,
a sec-pentyl group, a tert-pentyl group, a phenyl group, and a
naphthyl group; and an n-propyl group, an iso-propyl group, an
n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl
group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group,
a tert-pentyl group, a phenyl group, and a naphthyl group, each
substituted with at least one selected from deuterium, a
C.sub.1-C.sub.10 alkyl group, and a phenyl group.
4. The organometallic compound of claim 1, wherein R.sub.1 to
R.sub.6 are each independently selected from hydrogen, deuterium,
--F, a cyano group, a nitro group, --SF.sub.5, --CH.sub.3,
--CD.sub.3, --CD.sub.2H, --CDH.sub.2, --CF.sub.3, --CF.sub.2H,
--CFH.sub.2, groups represented by Formulae 9-1 to 9-19, groups
represented by Formulae 10-1 to 10-46, and
--Si(Q.sub.3)(Q.sub.4)(Q.sub.5): ##STR00096## ##STR00097##
##STR00098## ##STR00099## ##STR00100## ##STR00101## wherein in
Formulae 9-1 to 9-19 and 10-1 to 10-46, * indicates a binding site
to a neighboring atom.
5. An organometallic compound represented by Formula 1-1A:
##STR00102## wherein in Formula 1-1 .ANG., X.sub.1 is O or S,
T.sub.1 is a single bond, T.sub.2 is selected from a single bond,
*--O--*', *--S--*', *--C(R.sub.5)(R.sub.6)--*',
*--C(R.sub.5).dbd.C(R.sub.6)--*', *--C(.dbd.O)--*',
*--C(.dbd.S)--*', *--C.ident.C--*', *--N(R.sub.5)--*',
*--Si(R.sub.5)(R.sub.6)--*', and *--P(R.sub.5)(R.sub.6)--*',
wherein * and *' in each of the foregoing groups independently
indicate a binding site to a neighboring atom, b1 to b2 are 1,
X.sub.11 is N or C(R.sub.11), X.sub.12 is N or C(R.sub.12),
X.sub.13 is N or C(R.sub.13), X.sub.14 is N or C(R.sub.14),
X.sub.21 is N or C(R.sub.21), X.sub.22 is N or C(R.sub.22),
X.sub.23 is N or C(R.sub.23), X.sub.31 is N or C(R.sub.31),
X.sub.32 is N or C(R.sub.32), X.sub.33 is N or C(R.sub.33),
X.sub.41 is N or C(R.sub.41), X.sub.42 is N or C(R.sub.42),
X.sub.43 is N or C(R.sub.43), and X.sub.44 is N or C(R.sub.44),
R.sub.11 to R.sub.14, R.sub.21 to R.sub.23, R.sub.31 to R.sub.33,
and R.sub.41 to R.sub.44 are each independently selected from
hydrogen, deuterium, --F, --Cl, --Br, --I, --SF.sub.5, a hydroxy
group, a cyano group, a nitro group, a substituted or unsubstituted
C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted
C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted
C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted
C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted
C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or
unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or
unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl group, a
substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a
substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a
substituted or unsubstituted monovalent non-aromatic condensed
polycyclic group, a substituted or unsubstituted monovalent
non-aromatic condensed heteropolycyclic group,
--N(Q.sub.1)(Q.sub.2), --Si(Q.sub.3)(Q.sub.4)(Q.sub.5),
--B(Q.sub.6)(Q.sub.7), and --P(.dbd.O)(Q.sub.8)(Q.sub.9), two
groups selected from R.sub.11 to R.sub.14 are optionally connected
to each other to form a substituted or unsubstituted
C.sub.5-C.sub.30 carbocyclic group or a substituted or
unsubstituted C.sub.1-C.sub.30 heterocyclic group, two groups
selected from R.sub.21 to R.sub.23 are optionally connected to each
other to form a substituted or unsubstituted C.sub.5-C.sub.30
carbocyclic group or a substituted or unsubstituted
C.sub.1-C.sub.30 heterocyclic group, two groups selected from
R.sub.31 to R.sub.33 are optionally connected to each other to form
a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group
or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic
group, two groups selected from Ru to R.sub.44 are optionally
connected to each other to form a substituted or unsubstituted
C.sub.5-C.sub.30 carbocyclic group or a substituted or
unsubstituted C.sub.1-C.sub.30 heterocyclic group, two groups
selected from Ru to R.sub.14, R.sub.21 to R.sub.23, R.sub.31 to
R.sub.33, and R.sub.41 to R.sub.44 are optionally connected to each
other to form a substituted or unsubstituted C.sub.5-C.sub.30
carbocyclic group or a substituted or unsubstituted
C.sub.1-C.sub.30 heterocyclic group, T.sub.4 is C, Si, or P,
T.sub.5 is a group selected from a single bond, *--O--*', *--S--*',
*--C(R.sub.9)(R.sub.10)--*', *--C(R.sub.9).dbd.C(R.sub.10)--*',
*--C(.dbd.O)--*', *--C(.dbd.S)--*', *--N(R.sub.9)--*',
*--Si(R.sub.9)(R.sub.10)--*', and *--P(R.sub.9)(R.sub.10)--*',
wherein * and *' in each of the foregoing groups independently
indicate a binding site to a neighboring atom, R.sub.9 and R.sub.10
are each independently the same as R.sub.11, and CY.sub.5 and
CY.sub.6 are each independently selected from: a cyclopentane
group, a cyclohexane group, a cycloheptane group, a benzene group,
a naphthalene group, a fluorene group, a phenanthrene group, an
anthracene group, a triphenylene group, a pyrene group, a chrysene
group, a pyridine group, a pyrimidine group, a quinoline group, an
isoquinoline group, a quinazoline group, and a quinoxaline group;
and a cyclopentane group, a cyclohexane group, a cycloheptane
group, a benzene group, a naphthalene group, a fluorene group, a
phenanthrene group, an anthracene group, a triphenylene group, a
pyrene group, a chrysene group, a pyridine group, a pyrimidine
group, a quinoline group, an isoquinoline group, a quinazoline
group, and a quinoxaline group, each substituted with at least one
selected from deuterium, --F, --Cl, --Br, --I, --CD.sub.3,
--CD.sub.2H, --CDH.sub.2, --CF.sub.3, --CF.sub.2H, --CFH.sub.2, a
hydroxy group, a cyano group, a nitro group, a C.sub.1-C.sub.10
alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl
group, a phenyl group, a naphthyl group, a pyridinyl group, and a
pyrimidinyl group.
6. An organometallic compound selected from Compounds 1 to 78
below: ##STR00103## ##STR00104## ##STR00105## ##STR00106##
##STR00107## ##STR00108## ##STR00109## ##STR00110## ##STR00111##
##STR00112## ##STR00113## ##STR00114## ##STR00115## ##STR00116##
##STR00117## ##STR00118## ##STR00119## ##STR00120##
7. An organic light-emitting device comprising: a first electrode;
a second electrode; and an organic layer disposed between the first
electrode and the second electrode, wherein the organic layer
comprises an emission layer, and wherein the organic layer
comprises at least one organometallic compound of claim 1.
8. The organic light-emitting device of claim 7, wherein the first
electrode is an anode, the second electrode is a cathode, the
organic layer further comprises a hole transport region disposed
between the first electrode and the emission layer, and an electron
transport region disposed between the emission layer and the second
electrode, the hole transport region comprises a hole injection
layer, a hole transport layer, an electron blocking layer, or any
combination thereof, and the electron transport region comprises a
hole blocking layer, an electron transport layer, an electron
injection layer, or any combination thereof.
9. The organic light-emitting device of claim 7, wherein the
emission layer comprises the organometallic compound.
10. The organic light-emitting device of claim 9, wherein the
emission layer further comprises a host, and an amount of the host
is greater than an amount of the organometallic compound.
11. A diagnosis composition comprising at least one organometallic
compound of claim 1.
Description
CROSS-REFERENCE TO RELATED APPLICATION
This application claims priority to Korean Patent Application No.
10-2016-0015678, filed on Feb. 11, 2016, in the Korean Intellectual
Property Office, and all the benefits accruing therefrom under 35
U.S.C. .sctn. 119, the content of which is incorporated herein in
its entirety by reference.
BACKGROUND
1. Field
One or more embodiments relate to an organometallic compound, an
organic light-emitting device including the organometallic
compound, and a diagnosis composition including the organometallic
compound.
2. Description of the Related Art
Organic light-emitting devices (OLEDs) are self-emission devices
that have wide viewing angles, and short response times. OLEDs also
exhibit excellent brightness, driving voltage, and response speed
characteristics, and produce full-color images.
In an example, an organic light-emitting device includes an anode,
a cathode, and an organic layer that is disposed between the anode
and the cathode, wherein the organic layer includes an emission
layer. A hole transport region may be disposed between the anode
and the emission layer, and an electron transport region may be
disposed between the emission layer and the cathode. Holes provided
from the anode may move toward the emission layer through the hole
transport region, and electrons provided from the cathode may move
toward the emission layer through the electron transport region.
The holes and the electrons recombine in the emission layer to
produce excitons. These excitons transition from an excited state
to a ground state, thereby generating light.
Luminescent compounds, for example, phosphorescent luminescent
compounds may be used to monitor, sense, or detect biological
materials, such as cells or proteins.
Various types of organic light emitting devices are known. However,
there still remains a need in OLEDs having low driving voltage,
high efficiency, high brightness, and long lifespan.
SUMMARY
One or more embodiments include a novel organometallic compound, an
organic light-emitting device including the novel organometallic
compound, and a diagnosis composition including the novel
organometallic compound.
Additional aspects will be set forth in part in the description
which follows and, in part, will be apparent from the description,
or may be learned by practice of the presented embodiments.
According to one or more embodiments, an organometallic compound is
represented by Formula 1:
##STR00002##
In Formula 1,
X.sub.1 may be O or S,
X.sub.2 may be C, and
X.sub.3 and X.sub.4 may be N,
A bond between Pt and X.sub.1 and a bond between Pt and X.sub.2 may
be a covalent bond, and a bond between Pt and X.sub.3 and a bond
between Pt and X.sub.4 may be a coordinate bond,
Y.sub.1 and Y.sub.3 to Y.sub.8 may each independently be C or
N,
Y.sub.2 and Y.sub.9 may each independently be C, N, O, or S,
Y.sub.1 and Y.sub.2 may be connected to each other via a single
bond or a double bond, Y.sub.1 and Y.sub.3 may be connected to each
other via a single bond or a double bond, X.sub.2 and Y.sub.4 may
be connected to each other via a single bond or a double bond,
X.sub.2 and Y.sub.5 may be connected to each other via a single
bond or a double bond, X.sub.3 and Y.sub.6 may be connected to each
other via a single bond or a double bond, X.sub.3 and Y.sub.7 may
be connected to each other via a single bond or a double bond,
X.sub.4 and Y.sub.8 may be connected to each other via a single
bond or a double bond, and X.sub.4 and Y.sub.9 may be connected to
each other via a single bond or a double bond,
CY.sub.1 to CY.sub.4 may each independently be selected from a
C.sub.5-C.sub.30 carbocyclic group and a C.sub.1-C.sub.30
heterocyclic group,
T.sub.1 and T.sub.2 may each be a group independently be selected
from a single bond, *--O--*', *--S--*', *--C(R.sub.5)(R.sub.6)--*',
*--C(R.sub.5).dbd.*', *.dbd.O(R.sub.5)--*',
*--C(R.sub.5).dbd.C(R.sub.6)--*', *--C(.dbd.O)--*',
*--C(.dbd.S)--*', *--C.ident.C--*', *--N(R.sub.5)--*',
*--Si(R.sub.5)(R.sub.6)--*', and *--P(R.sub.5)(R.sub.6)--*',
wherein * and *' in each of the foregoing groups independently
indicate a binding site to a neighboring atom,
T.sub.3 may be a group selected from *--O--*', *--S--*',
*--C(R.sub.7)(R.sub.8)--*', *--C(R.sub.7).dbd.*',
*.dbd.C(R.sub.7)--*', *--C(R.sub.7).dbd.C(R.sub.8)--*',
*--C(.dbd.O)--*', *--C(.dbd.S)--*', *--C.ident.C--*',
*--N(R.sub.7)--*', *--Si(R.sub.7)(R.sub.8)--*', and
*--P(R.sub.7)(R.sub.8)--*', wherein * and *' in each of the
foregoing groups independently indicate a binding site to a
neighboring atom,
R.sub.5 and R.sub.6 may be optionally connected to each other via a
first linking group to form a substituted or unsubstituted
C.sub.5-C.sub.30 carbocyclic group or a substituted or
unsubstituted C.sub.1-C.sub.30 heterocyclic group,
R.sub.7 and R.sub.8 may be optionally connected to each other via a
second linking group to form a substituted or unsubstituted
C.sub.5-C.sub.30 carbocyclic group or a substituted or
unsubstituted C.sub.1-C.sub.30 heterocyclic group,
b1 to b3 may each independently be 1, 2, or 3,
R.sub.1 to R.sub.8 may each independently be selected from
hydrogen, deuterium, --F, --Cl, --Br, --I, --SF.sub.5, a hydroxyl
group, a cyano group, a nitro group, an amidino group, a hydrazine
group, a hydrazone group, a carboxylic acid group or a salt
thereof, a sulfonic acid group or a salt thereof, a phosphoric acid
group or a salt thereof, a substituted or unsubstituted
C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted
C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted
C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted
C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted
C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or
unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or
unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl group, a
substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a
substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a
substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a
substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a
substituted or unsubstituted monovalent non-aromatic condensed
polycyclic group, a substituted or unsubstituted monovalent
non-aromatic condensed heteropolycyclic group,
--N(Q.sub.1)(Q.sub.2), --Si(Q.sub.3)(Q.sub.4)(Q.sub.5),
--B(Q.sub.6)(Q.sub.7), and --P(.dbd.O)(Q.sub.8)(Q.sub.9),
a1 to a4 may each independently be 0, 1, 2, 3, 4, or 5,
two groups selected from groups R.sub.1 in the number of a1 may be
optionally connected to each other to form a substituted or
unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted
or unsubstituted C.sub.1-C.sub.30 heterocyclic group,
two groups selected from groups R.sub.2 in the number of a2 may be
optionally connected to each other to form a substituted or
unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted
or unsubstituted C.sub.1-C.sub.30 heterocyclic group,
two groups selected from groups R.sub.3 in the number of a3 may be
optionally connected to each other to form a substituted or
unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted
or unsubstituted C.sub.1-C.sub.30 heterocyclic group,
two groups selected from groups R.sub.4 in the number of a4 may be
optionally connected to each other to form a substituted or
unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted
or unsubstituted C.sub.1-C.sub.30 heterocyclic group,
two or more neighboring groups selected from R.sub.1 to R.sub.4 may
be optionally connected to each other to form a substituted or
unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted
or unsubstituted C.sub.1-C.sub.30 heterocyclic group,
at least one substituent selected from a substituent(s) of the
substituted C.sub.5-C.sub.30 carbocyclic group, the substituted
C.sub.1-C.sub.30 heterocyclic group, the substituted
C.sub.1-C.sub.60 alkyl group, the substituted C.sub.2-C.sub.60
alkenyl group, the substituted C.sub.2-C.sub.60 alkynyl group, the
substituted C.sub.1-C.sub.60 alkoxy group, the substituted
C.sub.3-C.sub.10 cycloalkyl group, the substituted heterocycloalkyl
group, the substituted C.sub.3-C.sub.10 cycloalkenyl group, the
substituted heterocycloalkenyl group, the substituted
C.sub.6-C.sub.60 aryl group, the substituted C.sub.6-C.sub.60
aryloxy group, the substituted C.sub.6-C.sub.60 arylthio group, the
substituted C.sub.1-C.sub.60 heteroaryl group, the substituted
monovalent non-aromatic condensed polycyclic group, and the
substituted monovalent non-aromatic condensed heteropolycyclic
group may be selected from:
deuterium, --F, --Cl, --Br, --I, --CD.sub.3, --CD.sub.2H,
--CDH.sub.2, --CF.sub.3, --CF.sub.2H, --CFH.sub.2, a hydroxyl
group, a cyano group, a nitro group, an amidino group, a hydrazine
group, a hydrazone group, a carboxylic acid group or a salt
thereof, a sulfonic acid group or a salt thereof, a phosphoric acid
group or a salt thereof, a C.sub.1-C.sub.60 alkyl group, a
C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group,
and a C.sub.1-C.sub.60 alkoxy group;
a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a
C.sub.2-C.sub.60 alkynyl group, and a C.sub.1-C.sub.60 alkoxy
group, each substituted with at least one selected from deuterium,
--F, --Cl, --Br, --I, --CD.sub.3, --CD.sub.2H, --CDH.sub.2,
--CF.sub.3, --CF.sub.2H, --CFH.sub.2, a hydroxyl group, a cyano
group, a nitro group, an amidino group, a hydrazine group, a
hydrazone group, a carboxylic acid group or a salt thereof, a
sulfonic acid group or a salt thereof, a phosphoric acid group or a
salt thereof, a C.sub.3-C.sub.10 cycloalkyl group, a
C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10
cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a
C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a
C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl
group, a monovalent non-aromatic condensed polycyclic group, a
monovalent non-aromatic condensed heteropolycyclic group,
--N(Q.sub.11)(Q.sub.12), --Si(Q.sub.13)(Q.sub.14)(Q.sub.15),
--B(Q.sub.16)(Q.sub.17), and --P(.dbd.O)(Q.sub.18)(Q.sub.19),
a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60
arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, and a monovalent
non-aromatic condensed heteropolycyclic group;
a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60
arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, and a monovalent
non-aromatic condensed heteropolycyclic group, each substituted
with at least one selected from deuterium, --F, --Cl, --Br, --I,
--CD.sub.3, --CD.sub.2H, --CDH.sub.2, --CF.sub.3, --CF.sub.2H,
--CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, an
amidino group, a hydrazine group, a hydrazone group, a carboxylic
acid group or a salt thereof, a sulfonic acid group or a salt
thereof, a phosphoric acid group or a salt thereof, a
C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a
C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a
C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a
C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group,
a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic
condensed polycyclic group, a monovalent non-aromatic condensed
heteropolycyclic group, --N(Q.sub.21)(Q.sub.22),
--Si(Q.sub.23)(Q.sub.24)(Q.sub.25), --B(Q.sub.26)(Q.sub.27), and
--P(.dbd.O)(Q.sub.28)(Q.sub.29); and --N(Q.sub.31)(Q.sub.32),
--Si(Q.sub.33)(Q.sub.34)(Q.sub.35), --B(Q.sub.36)(Q.sub.37), and
--P(.dbd.O)(Q.sub.38)(Q.sub.39),
wherein Q.sub.1 to Q.sub.9, Q.sub.11 to Q.sub.19, Q.sub.21 to
Q.sub.29, and Q.sub.31 to Q.sub.39 may each independently be
selected from hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl
group, a cyano group, a nitro group, an amidino group, a hydrazine
group, a hydrazone group, a carboxylic acid group or a salt
thereof, a sulfonic acid group or a salt thereof, a phosphoric acid
group or a salt thereof, a C.sub.1-C.sub.60 alkyl group, a
C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a
C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group,
a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10
cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a
C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryl group
substituted with at least one selected from a C.sub.1-C.sub.60
alkyl group and a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60
aryloxy group, a C.sub.6-C.sub.60 arylthio group, a
C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic
condensed polycyclic group, and a monovalent non-aromatic condensed
heteropolycyclic group.
According to one or more embodiments, an organic light-emitting
device includes:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the
second electrode,
wherein the organic layer including an emission layer, and
wherein the organic layer includes at least one organometallic
compound described above.
The organometallic compound in the emission layer may act as a
dopant.
According to one or more embodiments, a diagnosis composition
includes at least one organometallic compound represented by
Formula 1.
BRIEF DESCRIPTION OF THE DRAWING
These and/or other aspects will become apparent and more readily
appreciated from the following description of the embodiments,
taken in conjunction with FIGURE which is a schematic view of an
organic light-emitting device according to an embodiment.
DETAILED DESCRIPTION
Reference will now be made in detail to embodiments, examples of
which are illustrated in the accompanying drawings, wherein like
reference numerals refer to like elements throughout. In this
regard, the present embodiments may have different forms and should
not be construed as being limited to the descriptions set forth
herein. Accordingly, the embodiments are merely described below, by
referring to the figures, to explain aspects. As used herein, the
term "and/or" includes any and all combinations of one or more of
the associated listed items. Expressions such as "at least one of,"
when preceding a list of elements, modify the entire list of
elements and do not modify the individual elements of the list.
It will be understood that when an element is referred to as being
"on" another element, it can be directly in contact with the other
element or intervening elements may be present therebetween. In
contrast, when an element is referred to as being "directly on"
another element, there are no intervening elements present.
It will be understood that, although the terms first, second, third
etc. may be used herein to describe various elements, components,
regions, layers, and/or sections, these elements, components,
regions, layers, and/or sections should not be limited by these
terms. These terms are only used to distinguish one element,
component, region, layer, or section from another element,
component, region, layer, or section. Thus, a first element,
component, region, layer, or section discussed below could be
termed a second element, component, region, layer, or section
without departing from the teachings of the present
embodiments.
The terminology used herein is for the purpose of describing
particular embodiments only and is not intended to be limiting. As
used herein, the singular forms "a," "an," and "the" are intended
to include the plural forms as well, unless the context clearly
indicates otherwise.
The term "or" means "and/or." It will be further understood that
the terms "comprises" and/or "comprising," or "includes" and/or
"including" when used in this specification, specify the presence
of stated features, regions, integers, steps, operations, elements,
and/or components, but do not preclude the presence or addition of
one or more other features, regions, integers, steps, operations,
elements, components, and/or groups thereof.
Unless otherwise defined, all terms (including technical and
scientific terms) used herein have the same meaning as commonly
understood by one of ordinary skill in the art to which this
general inventive concept belongs. It will be further understood
that terms, such as those defined in commonly used dictionaries,
should be interpreted as having a meaning that is consistent with
their meaning in the context of the relevant art and the present
disclosure, and will not be interpreted in an idealized or overly
formal sense unless expressly so defined herein.
Exemplary embodiments are described herein with reference to cross
section illustrations that are schematic illustrations of idealized
embodiments. As such, variations from the shapes of the
illustrations as a result, for example, of manufacturing techniques
and/or tolerances, are to be expected. Thus, embodiments described
herein should not be construed as limited to the particular shapes
of regions as illustrated herein but are to include deviations in
shapes that result, for example, from manufacturing. For example, a
region illustrated or described as flat may, typically, have rough
and/or nonlinear features. Moreover, sharp angles that are
illustrated may be rounded. Thus, the regions illustrated in the
figures are schematic in nature and their shapes are not intended
to illustrate the precise shape of a region and are not intended to
limit the scope of the present claims.
"About" or "approximately" as used herein is inclusive of the
stated value and means within an acceptable range of deviation for
the particular value as determined by one of ordinary skill in the
art, considering the measurement in question and the error
associated with measurement of the particular quantity (i.e., the
limitations of the measurement system). For example, "about" can
mean within one or more standard deviations, or within .+-.30%,
20%, 10%, 5% of the stated value.
An organometallic compound according to an embodiment may be
represented by Formula 1:
##STR00003##
X.sub.1 in Formula 1 may be O or S. For example, X.sub.1 may be O,
but is not limited thereto.
In Formula 1, X.sub.2 may be C, and X.sub.3 and X.sub.4 may be
N.
In Formula 1, a bond between Pt and X.sub.1 and a bond between Pt
and X.sub.2 may be a covalent bond, and a bond between Pt and
X.sub.3 and a bond between Pt and X.sub.4 may be a coordinate
bond.
In Formula 1, Y.sub.1 and Y.sub.3 to Y.sub.8 may each independently
be C or N, and Y.sub.2 and Y.sub.9 may each independently be C, N,
O, or S.
In one or more embodiments, in Formula 1, X.sub.1 may be 0, and
Y.sub.1 and Y.sub.3 to Y.sub.8 may be C, but embodiments are not
limited thereto.
In Formula 1, Y.sub.1 and Y.sub.2 may be connected to each other
via a single bond or a double bond, Y.sub.1 and Y.sub.3 may be
connected to each other via a single bond or a double bond, X.sub.2
and Y.sub.4 may be connected to each other via a single bond or a
double bond, X.sub.2 and Y.sub.5 may be connected to each other via
a single bond or a double bond, X.sub.3 and Y.sub.6 may be
connected to each other via a single bond or a double bond, X.sub.3
and Y.sub.7 may be connected to each other via a single bond or a
double bond, X.sub.4 and Y.sub.9 may be connected to each other via
a single bond or a double bond, and X.sub.4 and Y.sub.9 may be
connected to each other via a single bond or a double bond.
CY.sub.1 to CY.sub.4 in Formula 1 may each independently be
selected from a C.sub.5-C.sub.30 carbocyclic group and a
C.sub.1-C.sub.30 heterocyclic group.
For example, CY.sub.1 and CY.sub.2 in Formula 1 may each
independently be selected from a benzene group, a naphthalene
group, an anthracene group, a phenanthrene group, a triphenylene
group, a pyrene group, a chrysene group, a cyclopentadiene group,
an indene group, a fluorene group, a pyrrole group, an indole
group, a carbazole group, a furan group, a benzofuran group, a
dibenzofuran group, a thiophene group, a benzothiophene group, a
dibenzothiophene group, a pyridine group, a pyrimidine group, and a
1,2,3,4-tetrahydronaphthalene group.
In one or more embodiments, CY.sub.3 and CY.sub.4 in Formula 1 may
each independently be selected from a pyridine group, a pyrimidine
group, a pyrazine group, a pyridazine group, a triazine group, a
quinoline group, an isoquinoline group, a quinoxaline group, a
quinazoline group, a phenanthroline group, a pyrazole group, an
imidazole group, a triazole group, an oxazole group, an iso-oxazole
group, a thiazole group, an isothiazole group, an oxadiazole group,
a thiadiazole group, a benzopyrazole group, a benzoimidazole group,
a benzoxazole group, a benzothiazole group, a benzooxadiazole
group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline
group, and a 5,6,7,8-tetrahydroquinoline group.
In one or more embodiments, in Formula 1, CY.sub.1 and CY.sub.2 may
each independently be a benzene group, a naphthalene group, a
fluorene group, a dibenzofuran group, or a dibenzothiophene group,
and
CY.sub.3 and CY.sub.4 may each independently be a pyridine group, a
pyrimidine group, a quinoline group, an isoquinoline group, a
quinoxaline group, a quinazoline group, a
5,6,7,8-tetrahydroisoquinoline group, or a
5,6,7,8-tetrahydroquinoline group.
In one or more embodiments, in Formula 1,
CY.sub.1 and CY.sub.2 may be a benzene group, and CY.sub.3 and
CY.sub.4 may be a pyridine group;
CY.sub.1 may be a benzene group, CY.sub.2 may be a naphthalene
group, a dibenzofuran group, or a dibenzothiophene group, and
CY.sub.3 and CY.sub.4 may be a pyridine group;
CY.sub.1 may be a naphthalene group, a dibenzofuran group, or a
dibenzothiophene group, CY.sub.2 may be a benzene group, and
CY.sub.3 and CY.sub.4 may be a pyridine group;
CY.sub.1 may be a dibenzofuran group or a dibenzothiophene group,
CY.sub.2 may be a naphthalene group, and CY.sub.3 and CY.sub.4 may
be a pyridine group;
CY.sub.1 and CY.sub.2 may be a benzene group, CY.sub.3 may be a
quinoline group, an isoquinoline group, a
5,6,7,8-tetrahydroisoquinoline group, or a
5,6,7,8-tetrahydroquinoline group, and CY.sub.4 may be a pyridine
group;
CY.sub.1 may be a benzene group, CY.sub.2 may be a naphthalene
group, CY.sub.3 may be a quinoline group, an isoquinoline group, a
5,6,7,8-tetrahydroisoquinoline group, or a
5,6,7,8-tetrahydroquinoline group, and CY.sub.4 may be a pyridine
group; or
CY.sub.1 and CY.sub.2 may be a benzene group, CY.sub.3 may be a
pyridine group, CY.sub.4 may be a quinoline group, an isoquinoline
group, a 5,6,7,8-tetrahydroisoquinoline group, or a
5,6,7,8-tetrahydroquinoline group, but embodiments are not limited
thereto.
In Formula 1, T.sub.1 and T.sub.2 may each be a group independently
be selected from a single bond, *--O--*', *--S--*',
*--C(R.sub.5)(R.sub.6)--*', *--C(R.sub.5).dbd.*',
*.dbd.C(R.sub.5)--*', *--C(R.sub.5).dbd.C(R.sub.6)--*',
*--C(.dbd.O)--*', *--C(.dbd.S)--*', *--C.ident.C--*',
*--N(R.sub.5)--*', *--Si(R.sub.5)(R.sub.6)--*', wherein * and *' in
each of the foregoing groups independently indicate a binding site
to a neighboring atom, and *--P(R.sub.5)(R.sub.6)--*', and T.sub.3
may be a group selected from *--O--*', *--S--*',
*--C(R.sub.7)(R.sub.8)--*', *--C(R.sub.7).dbd.*',
*.dbd.C(R.sub.7)--*', *--C(R.sub.7).dbd.C(R.sub.8)--*',
*--C(.dbd.O)--*', *--C(.dbd.S)--*', *--C.ident.C--*',
*--N(R.sub.7)--*', *--Si(R.sub.7)(R.sub.8)--*', and
*--P(R.sub.7)(R.sub.8)--*', wherein * and *' in each of the
foregoing groups independently indicate a binding site to a
neighboring atom. R.sub.5 to R.sub.8 are the same as described
below.
R.sub.5 and R.sub.6 may be optionally connected to each other via a
first linking group to form a substituted or unsubstituted
C.sub.6-C.sub.30 carbocyclic group or a substituted or
unsubstituted C.sub.1-C.sub.30 heterocyclic group, and R.sub.7 and
R.sub.8 may be optionally connected to each other via a second
linking group to form a substituted or unsubstituted
C.sub.5-C.sub.30 carbocyclic group or a substituted or
unsubstituted C.sub.1-C.sub.30 heterocyclic group.
The first linking group and the second linking group may each
independently be selected from a single bond, *--O--*',
*--C(R.sub.9)(R.sub.10)--*', *--C(R.sub.9).dbd.*',
*.dbd.C(R.sub.9)--*', *--C(R.sub.9).dbd.C(R.sub.10)--*',
*--C(.dbd.O)--*', *--C(.dbd.S)--*', *--C.ident.C--*',
*--N(R.sub.9)--*', *--Si(R.sub.9)(R.sub.10)--*', and
*--P(R.sub.9)(R.sub.10)--*', wherein * and *' in each of the
foregoing groups independently indicate a binding site to a
neighboring atom, and R.sub.9 and R.sub.10 are each independently
the same as described above in connection with R.sub.7.
In one or more embodiments, the first linking group and the second
linking group may each independently be selected from a single
bond, *--O--*', *--S--*', *--C(R.sub.9)(R.sub.10)--*',
*--N(R.sub.9)--*', *--Si(R.sub.9)(R.sub.10)--*', and
*--P(R.sub.9)(R.sub.10)--*', wherein * and *' in each of the
foregoing groups independently indicate a binding site to a
neighboring atom, but are not limited thereto.
b1 in Formula 1 indicates the number of groups T.sub.1 and may be
1, 2, or 3. When b1 is 2 or greater, two or more groups T.sub.1 may
be identical to or different from each other. b2 and b3 may be
understood by referring to the description provided in connection
with b1 and Formula 1.
b1 to b3 in Formula 1 may each independently be 1, 2, or 3. For
example, b1 to b3 in Formula 1 may be 1, but are not limited
thereto.
In one or more embodiments, in Formula 1, T.sub.1 may be a single
bond, T.sub.2 may be a group selected from a single bond, *--O--*',
*--C(R.sub.5)(R.sub.6)--*', *--N(R.sub.5)--*',
*--Si(R.sub.5)(R.sub.6)--*', and *--P(R.sub.5)(R.sub.6)--*',
wherein * and *' in each of the foregoing groups independently
indicate a binding site to a neighboring atom, and T.sub.3 may be a
group selected from *--C(R.sub.7)(R.sub.5)--*', *--N(R.sub.7)--*',
*--Si(R.sub.7)(R.sub.5)--*', and *--P(R.sub.7)(R.sub.5)--*',
wherein * and *' in each of the foregoing groups independently
indicate a binding site to a neighboring atom, but embodiments are
not limited thereto.
In one or more embodiments, in Formula 1, T.sub.3 may be a group
selected from *--C(R.sub.7)(R.sub.8)--*',
*--Si(R.sub.7)(R.sub.8)--*', and *--P(R.sub.7)(R.sub.8)--*',
wherein * and *' in each of the foregoing groups independently
indicate a binding site to a neighboring atom, b3 may be 1, and
R.sub.7 and R.sub.8 may be connected to each other via a second
linking group. The second linking group is the same as described
above.
R.sub.1 to R.sub.8 may each independently be selected from
hydrogen, deuterium, --F, --Cl, --Br, --I, --SF.sub.5, a hydroxyl
group, a cyano group, a nitro group, an amidino group, a hydrazine
group, a hydrazone group, a carboxylic acid group or a salt
thereof, a sulfonic acid group or a salt thereof, a phosphoric acid
group or a salt thereof, a substituted or unsubstituted
C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted
C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted
C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted
C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted
heterocycloalkyl group, a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted
heterocycloalkenyl group, a substituted or unsubstituted
C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted
C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted
C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted
C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted
monovalent non-aromatic condensed polycyclic group, a substituted
or unsubstituted monovalent non-aromatic condensed heteropolycyclic
group, --N(Q.sub.1)(Q.sub.2), --Si(Q.sub.3)(Q.sub.4)(Q.sub.5),
--B(Q.sub.6)(Q.sub.7), and --P(.dbd.O)(Q.sub.8)(Q.sub.9).
For example, R.sub.1 to R.sub.8 may each independently be selected
from:
hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amino group, an amidino group, a
hydrazine group, a hydrazone group, a carboxylic acid group or a
salt thereof, a sulfonic acid group or a salt thereof, a phosphoric
acid group or a salt thereof, --SF.sub.5, a C.sub.1-C.sub.20 alkyl
group, and a C.sub.1-C.sub.20 alkoxy group;
a C.sub.1-C.sub.20 alkyl group and a C.sub.1-C.sub.20 alkoxy group,
each substituted with at least one selected from deuterium, --F,
--Cl, --Br, --I, --CD.sub.3, --CD.sub.2H, --CDH.sub.2, --CF.sub.3,
--CF.sub.2H, --CFH.sub.2, a hydroxyl group, a cyano group, a nitro
group, an amino group, an amidino group, a hydrazine group, a
hydrazone group, a carboxylic acid group or a salt thereof, a
sulfonic acid group or a salt thereof, a phosphoric acid group or a
salt thereof, a C.sub.1-C.sub.10 alkyl group, a cyclopentyl group,
a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an
adamantanyl group, a norbornanyl group, a norbornenyl group, a
cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a
phenyl group, a naphthyl group, a pyridinyl group, and a
pyrimidinyl group;
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a
cyclooctyl group, an adamantanyl group, a norbornanyl group, a
norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a
cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl
group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl
group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a
pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl
group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group,
an oxazolyl group, an isoxazolyl group, a pyridinyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an
isoindolyl group, an indolyl group, an indazolyl group, a purinyl
group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group,
a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a
benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl
group, an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a
dibenzothiophenyl group, a benzocarbazolyl group, a
dibenzocarbazolyl group, an imidazopyridinyl group, and an
imidazopyrimidinyl group;
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a
cyclooctyl group, an adamantanyl group, a norbornanyl group, a
norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a
cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl
group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl
group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a
pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl
group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group,
an oxazolyl group, an isoxazolyl group, a pyridinyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an
isoindolyl group, an indolyl group, an indazolyl group, a purinyl
group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group,
a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a
benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl
group, an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a
dibenzothiophenyl group, a benzocarbazolyl group, a
dibenzocarbazolyl group, an imidazopyridinyl group, and an
imidazopyrimidinyl group, each substituted with at least one
selected from deuterium, --F, --Cl, --Br, --I, --CD.sub.3,
--CD.sub.2H, --CDH.sub.2, --CF.sub.3, --CF.sub.2H, --CFH.sub.2, a
hydroxyl group, a cyano group, a nitro group, an amino group, an
amidino group, a hydrazine group, a hydrazone group, a carboxylic
acid group or a salt thereof, a sulfonic acid group or a salt
thereof, a phosphoric acid group or a salt thereof, a
C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a
cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a
cyclooctyl group, an adamantanyl group, a norbornanyl group, a
norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a
cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl
group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl
group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a
pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl
group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group,
an oxazolyl group, an isoxazolyl group, a pyridinyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an
isoindolyl group, an indolyl group, an indazolyl group, a purinyl
group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group,
a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a
benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl
group, an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a
dibenzothiophenyl group, a benzocarbazolyl group, a
dibenzocarbazolyl group, an imidazopyridinyl group, and an
imidazopyrimidinyl group; and
--N(Q.sub.1)(Q.sub.2), --Si(Q.sub.3)(Q.sub.4)(Q.sub.5),
--B(Q.sub.6)(Q.sub.7), and --P(.dbd.O)(Q.sub.8)(Q.sub.9),
wherein Q.sub.1 to Q.sub.9 may each independently be selected
from:
--CH.sub.3, --CD.sub.3, --CD.sub.2H, --CDH.sub.2,
--CH.sub.2CH.sub.3, --CH.sub.2CD.sub.3, --CH.sub.2CD.sub.2H,
--CH.sub.2CDH.sub.2, --CHDCH.sub.3, --CHDCD.sub.2H, --CHDCDH.sub.2,
--CHDCD.sub.3, --CD.sub.2CD.sub.3, --CD.sub.2CD.sub.2H, and
--CD.sub.2CDH.sub.2,
an n-propyl group, an iso-propyl group, an n-butyl group, an
iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl
group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl
group, a phenyl group, and a naphthyl group; and
an n-propyl group, an iso-propyl group, an n-butyl group, an
iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl
group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl
group, a phenyl group, and a naphthyl group, each substituted with
at least one selected from deuterium, a C.sub.1-C.sub.10 alkyl
group, and a phenyl group.
In one or more embodiments, R.sub.1 to R.sub.8 may each
independently be selected from:
hydrogen, deuterium, --F, a cyano group, a nitro group, --SF.sub.5,
a methyl group, an ethyl group, an n-propyl group, an iso-propyl
group, an n-butyl group, an iso-butyl group, a sec-butyl group, a
tert-butyl group, an n-pentyl group, an iso-pentyl group, a
sec-pentyl group, a tert-pentyl group, an n-hexyl group, an
iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl
group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl
group, an n-octyl group, an iso-octyl group, a sec-octyl group, a
tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl
group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a
sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy
group, a propoxy group, a butoxy group, a pentoxy group, a
cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a
cyclooctyl group, an adamantanyl group, a norbornanyl group, a
norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a
cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl
group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl
group, and a dibenzothiophenyl group;
a methyl group, an ethyl group, an n-propyl group, an iso-propyl
group, an n-butyl group, an iso-butyl group, a sec-butyl group, a
tert-butyl group, an n-pentyl group, an iso-pentyl group, a
sec-pentyl group, a tert-pentyl group, an n-hexyl group, an
iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl
group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl
group, an n-octyl group, an iso-octyl group, a sec-octyl group, a
tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl
group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a
sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy
group, a propoxy group, a butoxy group, a pentoxy group, a
cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a
cyclooctyl group, an adamantanyl group, a norbornanyl group, a
norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a
cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl
group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl
group, and a dibenzothiophenyl group, each substituted with at
least one selected from deuterium, --F, --CD.sub.3, --CD.sub.2H,
--CDH.sub.2, --CF.sub.3, --CF.sub.2H, --CFH.sub.2, a cyano group, a
nitro group, a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10
alkoxy group, a cyclopentyl group, a cyclohexyl group, a
cycloheptyl group, a cyclooctyl group, an adamantanyl group, a
norbornanyl group, a norbornenyl group, a cyclopentenyl group, a
cyclohexenyl group, a cycloheptenyl group, a phenyl group, a
naphthyl group, a pyridinyl group, a pyrimidinyl group, a
carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl
group; and
--N(Q.sub.1)(Q.sub.2), --Si(Q.sub.3)(Q.sub.4)(Q.sub.5),
--B(Q.sub.6)(Q.sub.7), and --P(.dbd.O)(Q.sub.5)(Q.sub.9),
wherein Q.sub.1 to Q.sub.9 may each independently be selected
from:
--CH.sub.3, --CD.sub.3, --CD.sub.2H, --CDH.sub.2,
--CH.sub.2CH.sub.3, --CH.sub.2CD.sub.3, --CH.sub.2CD.sub.2H,
--CH.sub.2CDH.sub.2, --CHDCH.sub.3, --CHDCD.sub.2H, --CHDCDH.sub.2,
--CHDCD.sub.3, --CD.sub.2CD.sub.3, --CD.sub.2CD.sub.2H, and
--CD.sub.2CDH.sub.2;
an n-propyl group, an iso-propyl group, an n-butyl group, an
iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl
group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl
group, a phenyl group, and a naphthyl group; and
an n-propyl group, an iso-propyl group, an n-butyl group, an
iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl
group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl
group, a phenyl group, and a naphthyl group, each substituted with
at least one selected from deuterium, a C.sub.1-C.sub.10 alkyl
group, and a phenyl group,
but embodiments are not limited thereto.
In one or more embodiments, R.sub.1 to R.sub.8 may each
independently be selected from hydrogen, deuterium, --F, a cyano
group, a nitro group, --SF.sub.5, --CH.sub.3, --CD.sub.3,
--CD.sub.2H, --CDH.sub.2, --CF.sub.3, --CF.sub.2H, --CFH.sub.2,
groups represented by Formulae 9-1 to 9-19, groups represented by
Formulae 10-1 to 10-46, and --Si(Q.sub.3)(Q.sub.4)(Q.sub.5), but
are not limited thereto:
##STR00004## ##STR00005## ##STR00006## ##STR00007## ##STR00008##
##STR00009## ##STR00010## ##STR00011## ##STR00012##
In Formulae 9-1 to 9-19 and 10-1 to 10-46, * indicates a binding
site to a neighboring atom. Q.sub.3 to Q.sub.5 are the same as
described above.
a1 in Formula 1 indicates the number of groups R.sub.1 and may be
0, 1, 2, 3, 4, or 5. When a1 is 2 or greater, two or more groups
R.sub.1 may be identical to or different from each other. a2 to a4
may be understood by referring to the description provided in
connection with a1 and Formula 1.
a1 to a4 in Formula 1 may each independently be 0, 1, 2, 3, 4, or
5. In one or more embodiments, a1 to a4 may each independently be
0, 1, or 2, but are not limited thereto.
In Formula 1, two groups selected from groups R.sub.1 in the number
of a1 may be optionally connected to each other to form a
substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or
a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group,
two groups selected from groups R.sub.2 in the number of a2 may be
optionally connected to each other to form a substituted or
unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted
or unsubstituted C.sub.1-C.sub.30 heterocyclic group, two groups
selected from groups R.sub.3 in the number of a3 may be optionally
connected to each other to form a substituted or unsubstituted
C.sub.5-C.sub.30 carbocyclic group or a substituted or
unsubstituted C.sub.1-C.sub.30 heterocyclic group, and two groups
selected from groups R.sub.4 in the number of a4 may be optionally
connected to each other to form a substituted or unsubstituted
C.sub.5-C.sub.30 carbocyclic group or a substituted or
unsubstituted C.sub.1-C.sub.30 heterocyclic group. Examples of the
substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or
the substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic
group may include a substituted or unsubstituted pentadiene group,
a substituted or unsubstituted cyclohexane group, a substituted or
unsubstituted adamantane group, a substituted or unsubstituted
benzene group, a substituted or unsubstituted pyridine group, a
substituted or unsubstituted pyrimidine group, a substituted or
unsubstituted pyrazine group, a substituted or unsubstituted
pyridazine group, a substituted or unsubstituted naphthalene group,
a substituted or unsubstituted anthracene group, a substituted or
unsubstituted tetracene group, a substituted or unsubstituted
phenanthrene group, a substituted or unsubstituted
dihydronaphthalene group, a substituted or unsubstituted phenalene
group, a substituted or unsubstituted benzothiophene group, a
substituted or unsubstituted benzofuran group, a substituted or
unsubstituted indene group, and a substituted or unsubstituted
indole group.
In one or more embodiments, the organometallic compound may be
represented by Formula 1-1:
##STR00013##
In Formula 1-1,
X.sub.1, T.sub.1 to T.sub.3, and b1 to b3 are the same as described
above,
X.sub.11 may be N or C(R.sub.11), X.sub.12 may be N or C(R.sub.12),
X.sub.13 may be N or C(R.sub.13), X.sub.14 may be N or C(R.sub.14),
X.sub.21 may be N or C(R.sub.21), X.sub.22 may be N or C(R.sub.22),
X.sub.23 may be N or C(R.sub.23), X.sub.31 may be N or C(R.sub.31),
X.sub.32 may be N or C(R.sub.32), X.sub.33 may be N or C(R.sub.33),
X.sub.41 may be N or C(R.sub.41), X.sub.42 may be N or C(R.sub.42),
X.sub.43 may be N or C(R.sub.43), and X.sub.44 may be N or
C(R.sub.44),
R.sub.11 to R.sub.14 are each independently the same as described
above in connection with R.sub.1, and two groups selected from
R.sub.11 to R.sub.14 may be optionally connected to each other to
form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic
group or a substituted or unsubstituted C.sub.1-C.sub.30
heterocyclic group,
R.sub.21 to R.sub.23 are each independently the same as described
above in connection with R.sub.2, and two groups selected from
R.sub.21 to R.sub.23 may be optionally connected to each other to
form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic
group or a substituted or unsubstituted C.sub.1-C.sub.30
heterocyclic group,
R.sub.31 to R.sub.33 are each independently the same as described
above in connection with R.sub.3, and two groups selected from
R.sub.31 to R.sub.33 may be optionally connected to each other to
form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic
group or a substituted or unsubstituted C.sub.1-C.sub.30
heterocyclic group,
R.sub.41 to R.sub.44 are each independently the same as described
above in connection with R.sub.4, and two groups selected from
R.sub.41 to R.sub.44 may be optionally connected to each other to
form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic
group or a substituted or unsubstituted C.sub.1-C.sub.30
heterocyclic group, and
two groups selected from R.sub.11 to R.sub.14, R.sub.21 to
R.sub.23, R.sub.31 to R.sub.33, and R.sub.41 to R.sub.44 may be
optionally connected to each other to form a substituted or
unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted
or unsubstituted C.sub.1-C.sub.30 heterocyclic group.
In one or more embodiments, the organometallic compound may be
represented by Formula 1-1A:
##STR00014##
In Formula 1-1A,
T.sub.1, T.sub.2, b1, and b2 are the same as described above,
X.sub.11 to X.sub.14, X.sub.21 to X.sub.23, X.sub.31 to X.sub.33,
and X.sub.41 to X.sub.44 are the same as described above,
T.sub.4 may be C, Si, or P,
T.sub.5 may be selected from a single bond, *--O--*', *--S--*',
*--C(R.sub.9)(R.sub.10)--*', *--C(R.sub.9).dbd.*',
*.dbd.C(R.sub.9)--*', *--C(R.sub.9).dbd.C(R.sub.10)--*',
*--C(.dbd.O)--*', *--C(.dbd.S)--*' *--C.ident.C--*',
*--N(R.sub.9)--*', *--Si(R.sub.9)(R.sub.10)--*', and
*--P(R.sub.9)(R.sub.10)--*', wherein * and *' in each of the
foregoing groups independently indicate a binding site to a
neighboring atom,
R.sub.9 and R.sub.10 are each independently the same as described
above in connection with R.sub.7, and
CY.sub.5 and CY.sub.6 may each independently be selected from: a
cyclopentane group, a cyclohexane group, a cycloheptane group, a
benzene group, a naphthalene group, a fluorene group, a
phenanthrene group, an anthracene group, a triphenylene group, a
pyrene group, a chrysene group, a pyridine group, a pyrimidine
group, a quinoline group, an isoquinoline group, a quinazoline
group, and a quinoxaline group; and
a cyclopentane group, a cyclohexane group, a cycloheptane group, a
benzene group, a naphthalene group, a fluorene group, a
phenanthrene group, an anthracene group, a triphenylene group, a
pyrene group, a chrysene group, a pyridine group, a pyrimidine
group, a quinoline group, an isoquinoline group, a quinazoline
group, and a quinoxaline group, each substituted with at least one
selected from deuterium, --F, --Cl, --Br, --I, --CD.sub.3,
--CD.sub.2H, --CDH.sub.2, --CF.sub.3, --CF.sub.2H, --CFH.sub.2, a
hydroxyl group, a cyano group, a nitro group, an amino group, an
amidino group, a hydrazine group, a hydrazone group, a carboxylic
acid group or a salt thereof, a sulfonic acid group or a salt
thereof, a phosphoric acid group or a salt thereof, a
C.sub.1-C.sub.10 alkyl group, a cyclopentyl group, a cyclohexyl
group, a cycloheptyl group, a phenyl group, a naphthyl group, a
pyridinyl group, and a pyrimidinyl group,
but embodiments are not limited thereto.
In one or more embodiments, the organometallic compound may be
represented by one selected from Formulae 1(1) to 1(41):
##STR00015## ##STR00016## ##STR00017## ##STR00018## ##STR00019##
##STR00020## ##STR00021## ##STR00022## ##STR00023## ##STR00024##
##STR00025## ##STR00026## ##STR00027## ##STR00028## ##STR00029##
##STR00030## ##STR00031##
In Formulae 1(1) to 1(41),
X.sub.1, T.sub.1 to T.sub.3, and b1 to b3 are the same as described
above,
R.sub.11 to R.sub.14 are each independently the same as described
above in connection with R.sub.1,
R.sub.21 to R.sub.23 are each independently the same as described
above in connection with R.sub.2,
R.sub.31 to R.sub.33 are each independently the same as described
above in connection with R.sub.3,
R.sub.41 to R.sub.44 are each independently the same as described
above in connection with R.sub.4,
X.sub.11 may be O or S,
R.sub.51 to R.sub.54 are each independently the same as described
above in connection with R.sub.1,
T.sub.11 may be a group selected from *--O--*', *--S--*',
*--C(R.sub.61)(R.sub.62)--*', *--C(R.sub.61).dbd.*',
*.dbd.C(R.sub.61)--*', *--C(R.sub.61).dbd.C(R.sub.62)--*',
*--C(.dbd.O)--*', *--C(.dbd.S)--*', *--C.ident.C--*',
*--N(R.sub.61)--*', *--Si(R.sub.61)(R.sub.62)--*', and
*--P(R.sub.61)(R.sub.62)--*', wherein * and *' in each of the
foregoing groups independently indicate a binding site to a
neighboring atom,
R.sub.61 and R.sub.62 are each independently the same as described
above in connection with R.sub.7, and
b11 may be 1, 2, or 3.
For example, in Formulae 1-1, 1-1A, and 1(1) to 1(41),
T.sub.1 may be a single bond,
T.sub.2 may be a group selected from a single bond, *--O--*',
*--S--*', *--C(R.sub.5)(R.sub.6)--*', *--N(R.sub.5)--*',
*--Si(R.sub.5)(R.sub.6)--*', and *--P(R.sub.5)(R.sub.6)--*',
wherein * and *' in each of the foregoing groups independently
indicate a binding site to a neighboring atom,
T.sub.3 may be a group selected from *--O--*', *--S--*',
*--C(R.sub.7)(R.sub.8)--*', *--N(R.sub.7)--*',
*--Si(R.sub.7)(R.sub.8)--*', and *--P(R.sub.7)(R.sub.8)--*',
wherein * and *' in each of the foregoing groups independently
indicate a binding site to a neighboring atom,
b1 to b3 may be 1, and
R.sub.5 to R.sub.8, R.sub.11 to R.sub.14, R.sub.21 to R.sub.23,
R.sub.31 to R.sub.33, R.sub.41 to R.sub.44, R.sub.51 to R.sub.54,
R.sub.61, and R.sub.62 may each independently be selected from
hydrogen, deuterium, --F, a cyano group, a nitro group, --SF.sub.5,
--CH.sub.3, --CD.sub.3, --CD.sub.2H, --CDH.sub.2, --CF.sub.3,
--CF.sub.2H, --CFH.sub.2, groups represented by Formulae 9-1 to
9-19, groups represented by Formulae 10-1 to 10-46, and
--Si(Q.sub.3)(Q.sub.4)(Q.sub.5), but are not limited thereto.
Q.sub.3 to Q.sub.5 are the same as described above.
In one or more embodiments, in Formulae 1-1 and 1-1A, a) two groups
selected from R.sub.11 to R.sub.14, b) two groups selected from
R.sub.21 to R.sub.23, c) two groups selected from R.sub.31 to
R.sub.33, or d) two groups selected from R.sub.41 to R.sub.44 may
be optionally connected to each other to form one selected
from:
a cyclopentane group, a cyclohexane group, an adamantane group, a
norbornane group, a benzene group, a pyridine group, a pyrimidine
group, a naphthalene group, a pyrene group, and a chrysene group;
and
a cyclopentane group, a cyclohexane group, an adamantane group, a
norbornane group, a benzene group, a pyridine group, a pyrimidine
group, a naphthalene group, a pyrene group, and a chrysene group,
each substituted with at least one selected from deuterium, --F,
--CD.sub.3, --CD.sub.2H, --CDH.sub.2, --CF.sub.3, --CF.sub.2H,
--CFH.sub.2, a cyano group, a nitro group, a C.sub.1-C.sub.10 alkyl
group, a C.sub.1-C.sub.10 alkoxy group, a cyclopentyl group, a
cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an
adamantanyl group, a norbornanyl group, a norbornenyl group, a
cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a
phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl
group, a dibenzofuranyl group, and a dibenzothiophenyl group,
but embodiments are not limited thereto.
In one or more embodiments, the organometallic compound may be one
selected from Compounds 1 to 78, but is not limited thereto:
##STR00032## ##STR00033## ##STR00034## ##STR00035## ##STR00036##
##STR00037## ##STR00038## ##STR00039## ##STR00040## ##STR00041##
##STR00042## ##STR00043## ##STR00044## ##STR00045## ##STR00046##
##STR00047## ##STR00048## ##STR00049## ##STR00050##
##STR00051##
In Formula 1, X.sub.1 may be O or S, X.sub.2 may be C, and X.sub.3
and X.sub.4 may be N. Therefore, the highest occupied molecular
orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO)
may be effectively separated within a molecule of the
organometallic compound represented by Formula 1, thereby improving
efficiency of an electronic device, for example, an organic
light-emitting device including the compound represented by Formula
1.
In addition, T.sub.3 in Formula 1 may be a group selected from
*--O--*', *--S--*', *--C(R.sub.7)(R.sub.8)--*'
*--C(R.sub.7).dbd.*', *.dbd.C(R.sub.7)--*',
*--C(R.sub.7).dbd.C(R.sub.8)--*', *--C(.dbd.O)--*',
*--C(.dbd.S)--*', *--C.ident.C--*', *--N(R.sub.7)--*',
*--Si(R.sub.7)(R.sub.8)--*', and *--P(R.sub.7)(R.sub.8)--*',
wherein * and *' in each of the foregoing groups independently
indicate a binding site to a neighboring atom. That is, T.sub.3 in
Formula 1 may not be a single bond. Therefore, a self-quenching
reduction group may be introduced to Formula 1 (that is, T.sub.3 in
Formula 1 may act as the self-quenching reduction group), thereby
reducing a roll-off ratio of an electronic device, for example, an
organic light-emitting device including the compound represented by
Formula 1, and improving efficiency thereof.
For example, the HOMO, the LUMO, a singlet (Si) energy level, and a
triplet (T.sub.1) energy level of Compounds 1, 2, 3, 5, 8, 10, 12,
15, 36, 44, and 66 and Compounds A and B below were evaluated by
using a Gaussian program density functional theory (DFT) method
(the structure was optimized at B3LYP, 6-31G(d,p) level). Results
thereof are shown in Table 1.
TABLE-US-00001 TABLE 1 HOMO LUMO S.sub.1 energy level T.sub.1
energy level Compound No. (eV) (eV) (eV) (eV) 1 -4.440 -1.636 2.233
2.028 2 -4.405 -1.607 2.224 2.021 3 -4.478 -1.680 2.221 2.020 5
-4.475 -1.677 2.220 2.019 8 -4.446 -1.647 2.220 2.019 10 -4.369
-1.625 2.184 1.985 12 -4.374 -1.639 2.170 1.974 15 -4.400 -1.634
2.214 1.985 36 -4.378 -1.716 2.136 1.965 44 -4.332 -1.599 2.152
1.964 66 -4.532 -1.921 2.082 1.879 A -4.782 -1.521 2.678 2.443 B
-4.704 -2.538 1.662 1.485
##STR00052##
Based on the results of Table 1, it is determined that the
organometallic compound represented by Formula 1 has electric
characteristics that are suitable for use in an electronic device,
for example, for use as a dopant of an organic light-emitting
device.
Synthesis methods of the organometallic compound represented by
Formula 1 may be recognizable by one of ordinary skill in the art
by referring to Synthesis Examples provided below.
The organometallic compound represented by Formula 1 is suitable
for use in an organic layer of an organic light-emitting device,
for example, for use as a dopant in an emission layer of the
organic layer. Thus, another aspect provides an organic
light-emitting device that includes:
a first electrode;
a second electrode; and
an organic layer that is disposed between the first electrode and
the second electrode,
wherein the organic layer includes an emission layer and at least
one organometallic compound represented by Formula 1.
The organic light-emitting device may have, due to the inclusion of
an organic layer including the organometallic compound represented
by Formula 1, low driving voltage, high efficiency, high power,
high quantum efficiency, a long lifespan, a low roll-off ratio, and
excellent color purity.
The organometallic compound of Formula 1 may be used between a pair
of electrodes of an organic light-emitting device. For example, the
organometallic compound represented by Formula 1 may be included in
the emission layer. In this regard, the organometallic compound may
act as a dopant, and the emission layer may further include a host
(that is, an amount of the organometallic compound represented by
Formula 1 is smaller than an amount of the host).
The expression that "(an organic layer) includes at least one
organometallic compound" as used herein may refer to an embodiment
in which "(an organic layer) includes identical organometallic
compounds represented by Formula 1 and an embodiment in which (an
organic layer) includes two or more different organometallic
compounds represented by Formula 1.
For example, the organic layer may include only Compound 1 as the
organometallic compound. In this regard, Compound 1 may be included
only in the emission layer of the organic light-emitting device. In
one or more embodiments, the organic layer may include, as the
organometallic compound, Compound 1 and Compound 2. In this regard,
Compound 1 and Compound 2 may be included in the same layer (for
example, Compound 1 and Compound 2 all may be included in an
emission layer).
The first electrode may be an anode, which is a hole injection
electrode, and the second electrode may be a cathode, which is an
electron injection electrode; or the first electrode may be a
cathode, which is an electron injection electrode, and the second
electrode may be an anode, which is a hole injection electrode.
For example, regarding the organic light-emitting device, the first
electrode may be an anode, and the second electrode may be a
cathode, and the organic layer may further include a hole transport
region disposed between the first electrode and the emission layer,
and an electron transport region disposed between the emission
layer and the second electrode, and the hole transport region may
include a hole injection layer, a hole transport layer, an electron
blocking layer, or any combination thereof, and the electron
transport region may include a hole blocking layer, an electron
transport layer, an electron injection layer, or any combination
thereof.
The term "organic layer" as used herein refers to a single layer
and/or a plurality of layers disposed between the first electrode
and the second electrode of the organic light-emitting device. The
"organic layer" may include, in addition to an organic compound, an
organometallic complex including a metal.
FIGURE is a schematic view of an organic light-emitting device 10
according to an embodiment. Hereinafter, the structure of an
organic light-emitting device according to an embodiment and a
method of manufacturing an organic light-emitting device according
to an embodiment will be described in connection with FIGURE. The
organic light-emitting device 10 includes a first electrode 11, an
organic layer 15, and a second electrode 19, which are sequentially
stacked in this stated order.
A substrate may be additionally disposed under the first electrode
11 or above the second electrode 19. For use as the substrate, any
substrate that is used in general organic light-emitting devices
may be used, and the substrate may be a glass substrate or a
transparent plastic substrate, each having excellent mechanical
strength, thermal stability, transparency, surface smoothness, ease
of handling, and water-resistance.
The first electrode 11 may be formed by depositing or sputtering a
material for forming the first electrode 11 on the substrate. The
first electrode 11 may be an anode. The material for forming the
first electrode 11 may be selected from materials with a high work
function to facilitate hole injection. The first electrode 11 may
be a reflective electrode, a semi-transmissive electrode, or a
transmissive electrode. The material for forming the first
electrode 11 may be, for example, indium tin oxide (ITO), indium
zinc oxide (IZO), tin oxide (SnO.sub.2), and zinc oxide (ZnO). In
one or more embodiments, magnesium (Mg), aluminum (Al),
aluminum-lithium (Al--Li), calcium (Ca), magnesium-indium (Mg--In),
or magnesium-silver (Mg--Ag) may be used as the material for
forming the first electrode 11.
The first electrode 11 may have a single-layered structure or a
multi-layered structure including two or more layers. For example,
the first electrode 11 may have a three-layered structure of
ITO/Ag/ITO, but the structure of the first electrode 110 is not
limited thereto.
The organic layer 15 is disposed on the first electrode 11.
The organic layer 15 may include a hole transport region, an
emission layer, and an electron transport region.
The hole transport region may be disposed between the first
electrode 11 and the emission layer.
The hole transport region may include a hole injection layer, a
hole transport layer, an electron blocking layer, a buffer layer,
or any combination thereof.
The hole transport region may include only either a hole injection
layer or a hole transport layer. In one or more embodiments, the
hole transport region may have a structure of hole injection
layer/hole transport layer or hole injection layer/hole transport
layer/electron blocking layer, which are sequentially stacked in
this stated order from the first electrode 11.
A hole injection layer may be formed on the first electrode 11 by
using one or more suitable methods selected from vacuum deposition,
spin coating, casting, or Langmuir-Blodgett (LB) deposition.
When a hole injection layer is formed by vacuum deposition, the
deposition conditions may vary according to a material that is used
to form the hole injection layer, and the structure and thermal
characteristics of the hole injection layer. For example, the
deposition conditions may include a deposition temperature of about
100.degree. C. to about 500.degree. C., a vacuum pressure of about
10.sup.-8 torr to about 10.sup.-3 torr, and a deposition rate of
about 0.01 .ANG./sec to about 100 .ANG./sec. However, the
deposition conditions are not limited thereto.
When the hole injection layer is formed using spin coating, coating
conditions may vary according to the material used to form the hole
injection layer, and the structure and thermal properties of the
hole injection layer. For example, a coating speed may be from
about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and a
temperature at which a heat treatment is performed to remove a
solvent after coating may be from about 80.degree. C. to about
200.degree. C. However, the coating conditions are not limited
thereto.
Conditions for forming a hole transport layer and an electron
blocking layer may be understood by referring to conditions for
forming the hole injection layer.
The hole transport region may include at least one selected from
m-MTDATA, TDATA, 2-TNATA, NPB, .beta.-NPB, TPD, Spiro-TPD,
Spiro-NPB, methylated-NPB, TAPC, HMTPD,
4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA),
polyaniline/dodecylbenzene sulfonic acid (Pani/DBSA),
poly(3,4-ethylenedioxythiophene)/poly(4-styrene sulfonate)
(PEDOT/PSS), polyaniline/camphor sulfonic acid (Pani/CSA),
polyaniline/poly(4-styrene sulfonate) (Pani/PSS), a compound
represented by Formula 201 below, and a compound represented by
Formula 202 below:
##STR00053## ##STR00054## ##STR00055## ##STR00056##
Ar.sub.101 and Ar.sub.102 in Formula 201 may each independently be
selected from:
a phenylene group, a pentalenylene group, an indenylene group, a
naphthylene group, an azulenylene group, a heptalenylene group, an
acenaphthylene group, a fluorenylene group, a phenalenylene group,
a phenanthrenylene group, an anthracenylene group, a
fluoranthenylene group, a triphenylenylene group, a pyrenylene
group, a chrysenylenylene group, a naphthacenylene group, a
picenylene group, a perylenylene group, and a pentacenylene group;
and
a phenylene group, a pentalenylene group, an indenylene group, a
naphthylene group, an azulenylene group, a heptalenylene group, an
acenaphthylene group, a fluorenylene group, a phenalenylene group,
a phenanthrenylene group, an anthracenylene group, a
fluoranthenylene group, a triphenylenylene group, a pyrenylene
group, a chrysenylenylene group, a naphthacenylene group, a
picenylene group, a perylenylene group, and a pentacenylene group,
each substituted with at least one selected from deuterium, --F,
--Cl, --Br, --I, a hydroxyl group, a cyano group, a nitro group, an
amino group, an amidino group, a hydrazine group, a hydrazone
group, a carboxylic acid group or a salt thereof, a sulfonic acid
group or a salt thereof, a phosphoric acid group or a salt thereof,
a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a
C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a
C.sub.3-C.sub.10 cycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl
group, a heterocycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a
C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group,
a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic
condensed polycyclic group, and a monovalent non-aromatic condensed
heteropolycyclic group.
In Formula 201, xa and xb may each independently be an integer
selected from 0 to 5, or 0, 1, or 2. For example, xa is 1 and xb is
0, but xa and xb are not limited thereto.
R.sub.101 to R.sub.108, R.sub.111 to R.sub.119, and R.sub.121 to
R.sub.124 in Formulae 201 and 202 may each independently be
selected from:
hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amino group, an amidino group, a
hydrazine group, a hydrazone group, a carboxylic acid group or a
salt thereof, a sulfonic acid group or a salt thereof, a phosphoric
acid group or a salt thereof, a C.sub.1-C.sub.10 alkyl group (for
example, a methyl group, an ethyl group, a propyl group, a butyl
group, a pentyl group, a hexyl group, and so on), and a
C.sub.1-C.sub.10 alkoxy group (for example, a methoxy group, an
ethoxy group, a propoxy group, a butoxy group, a pentoxy group, and
so on);
a C.sub.1-C.sub.10 alkyl group and a C.sub.1-C.sub.10 alkoxy group,
each substituted with at least one selected from deuterium, --F,
--Cl, --Br, --I, a hydroxyl group, a cyano group, a nitro group, an
amino group, an amidino group, a hydrazine group, a hydrazone
group, a carboxylic acid group or a salt thereof, a sulfonic acid
group or a salt thereof, and a phosphoric acid group or a salt
thereof;
a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl
group, and a pyrenyl group; and
a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl
group, and a pyrenyl group, each substituted with at least one
selected from deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amino group, an amidino group, a
hydrazine group, a hydrazone group, a carboxylic acid group or a
salt thereof, a sulfonic acid group or a salt thereof, a phosphoric
acid group or a salt thereof, a C.sub.1-C.sub.10 alkyl group and
C.sub.1-C.sub.10 alkoxy group, but are not limited thereto.
R.sub.109 in Formula 201 may be selected from:
a phenyl group, a naphthyl group, an anthracenyl group, and a
pyridinyl group; and
a phenyl group, a naphthyl group, an anthracenyl group, and a
pyridinyl group, each substituted with at least one selected from
deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a cyano group, a
nitro group, an amino group, an amidino group, a hydrazine group, a
hydrazone group, a carboxylic acid group or a salt thereof, a
sulfonic acid group or a salt thereof, a phosphoric acid group or a
salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a phenyl group, a naphthyl group, an anthracenyl
group, and a pyridinyl group.
In one or more embodiments, the compound represented by Formula 201
may be represented by Formula 201A, but is not limited thereto:
##STR00057##
R.sub.101, R.sub.111, R.sub.112, and R.sub.109 in Formula 201A may
be the same as described above.
For example, the compound represented by Formula 201, and the
compound represented by Formula 202 may include compounds HT1 to
HT20 illustrated below, but are not limited thereto:
##STR00058## ##STR00059## ##STR00060## ##STR00061## ##STR00062##
##STR00063## ##STR00064##
A thickness of the hole transport region may be in a range of about
100 .ANG. to about 10,000 .ANG., for example, about 100 .ANG. to
about 1,000 .ANG.. While not wishing to be bound by theory, it is
understood that when the hole transport region includes at least
one of a hole injection layer and a hole transport layer, the
thickness of the hole injection layer may be in a range of about
100 .ANG. to about 10,000 .ANG., and for example, about 100 .ANG.
to about 1,000 .ANG., and the thickness of the hole transport layer
may be in a range of about 50 .ANG. to about 2,000 .ANG., and for
example, about 100 .ANG. to about 1,500 .ANG.. While not wishing to
be bound by theory, it is understood that when the thicknesses of
the hole transport region, the hole injection layer, and the hole
transport layer are within these ranges, satisfactory hole
transporting characteristics may be obtained without a substantial
increase in driving voltage.
The hole transport region may further include, in addition to these
materials, a charge-generation material for the improvement of
conductive properties. The charge-generation material may be
homogeneously or non-homogeneously dispersed in the hole transport
region.
The charge-generation material may be, for example, a p-dopant. The
p-dopant may be one selected from a quinone derivative, a metal
oxide, and a cyano group-containing compound, but embodiments are
not limited thereto. Non-limiting examples of the p-dopant include
a quinone derivative, such as tetracyanoquinonedimethane (TCNQ) or
2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ);
a metal oxide, such as a tungsten oxide or a molybdenium oxide; and
a cyano group-containing compound, such as Compound HT-D1 below,
but are not limited thereto:
##STR00065##
The hole transport region may include a buffer layer.
Also, the buffer layer may compensate for an optical resonance
distance according to a wavelength of light emitted from the
emission layer, and thus, the efficiency of a formed organic
light-emitting device may be improved.
Then, an emission layer may be formed on the hole transport region
by vacuum deposition, spin coating, casting, LB deposition, or the
like. When the emission layer is formed by vacuum deposition or
spin coating, the deposition or coating conditions may be similar
to those applied to form the hole injection layer although the
deposition or coating conditions may vary according to the material
that is used to form the emission layer.
Meanwhile, when the hole transport region includes an electron
blocking layer, a material for the electron blocking layer may be
selected from materials for the hole transport region described
above and materials for a host to be explained later. However, the
material for the electron blocking layer is not limited thereto.
For example, when the hole transport region includes an electron
blocking layer, a material for the electron blocking layer may be
mCP, which will be explained later.
The emission layer may include a host and a dopant, and the dopant
may include the organometallic compound represented by Formula
1.
The host may include at least one selected from TPBi, TBADN, ADN
(also referred to as "DNA"), CBP, CDBP, TCP, mCP, Compound H50, and
Compound H51:
##STR00066## ##STR00067##
In one or more embodiments, the host may further include a compound
represented by Formula 301 below.
##STR00068##
Ar.sub.111 and Ar.sub.112 in Formula 301 may each independently be
selected from:
a phenylene group, a naphthylene group, a phenanthrenylene group,
and a pyrenylene group; and
a phenylene group, a naphthylene group, a phenanthrenylene group,
and a pyrenylene group, each substituted with at least one selected
from a phenyl group, a naphthyl group, and an anthracenyl
group.
Ar.sub.113 to Ar.sub.116 in Formula 301 may each independently be
selected from:
a C.sub.1-C.sub.10 alkyl group, a phenyl group, a naphthyl group, a
phenanthrenyl group, and a pyrenyl group; and
a phenyl group, a naphthyl group, a phenanthrenyl group, and a
pyrenyl group, each substituted with at least one selected from a
phenyl group, a naphthyl group, and an anthracenyl group.
g, h, i, and j in Formula 301 may each independently be an integer
selected from 0 to 4, and may be, for example, 0, 1, or 2.
Ar.sub.113 to Ar.sub.116 in Formula 301 may each independently be
selected from:
a C.sub.1-C.sub.10 alkyl group, substituted with at least one
selected from a phenyl group, a naphthyl group, and an anthracenyl
group;
a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl
group, a phenanthrenyl group, and a fluorenyl group;
a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl
group, a phenanthrenyl group, and a fluorenyl group, each
substituted with at least one selected from deuterium, --F, --Cl,
--Br, --I, a hydroxyl group, a cyano group, a nitro group, an amino
group, an amidino group, a hydrazine group, a hydrazone group, a
carboxylic acid group or a salt thereof, a sulfonic acid group or a
salt thereof, a phosphoric acid group or a salt thereof, a
C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a
C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a
phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl
group, a phenanthrenyl group, and a fluorenyl group; and
##STR00069##
but embodiments are not limited thereto.
In one or more embodiments, the host may include a compound
represented by Formula 302 below:
##STR00070##
Ar.sub.122 to Ar.sub.125 in Formula 302 are the same as described
in detail in connection with Ar.sub.113 in Formula 301.
Ar.sub.126 and Ar.sub.127 in Formula 302 may each independently be
a C.sub.1-C.sub.10 alkyl group (for example, a methyl group, an
ethyl group, or a propyl group).
k and l in Formula 302 may each independently be an integer
selected from 0 to 4. For example, k and l may be 0, 1, or 2.
The compound represented by Formula 301 and the compound
represented by Formula 302 may include Compounds H1 to H42
illustrated below, but are not limited thereto:
##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075##
##STR00076## ##STR00077## ##STR00078## ##STR00079##
When the organic light-emitting device is a full-color organic
light-emitting device, the emission layer may be patterned into a
red emission layer, a green emission layer, and a blue emission
layer. In one or more embodiments, due to a stack structure
including a red emission layer, a green emission layer, and/or a
blue emission layer, the emission layer may emit white light.
When the emission layer includes a host and a dopant, an amount of
the dopant may be in a range of about 0.01 parts to about 15 parts
by weight based on 100 parts by weight of the host, but is not
limited thereto.
A thickness of the emission layer may be in a range of about 100
.ANG. to about 1,000 .ANG., for example, about 200 .ANG. to about
600 .ANG.. While not wishing to be bound by theory, it is
understood that when the thickness of the emission layer is within
the above ranges, excellent light-emission characteristics may be
obtained without a substantial increase in driving voltage.
Then, an electron transport region may be disposed on the emission
layer.
The electron transport region may include a hole blocking layer, an
electron transport layer, an electron injection layer, or any
combination thereof.
For example, the electron transport region may have a structure of
hole blocking layer/electron transport layer/electron injection
layer or a structure of electron transport layer/electron injection
layer, but the structure of the electron transport region is not
limited thereto. The electron transport layer may have a
single-layered structure or a multi-layered structure including two
or more different materials.
Conditions for forming the hole blocking layer, the electron
transport layer, and the electron injection layer which constitute
the electron transport region may be understood by referring to the
conditions for forming the hole injection layer.
When the electron transport region includes a hole blocking layer,
the hole blocking layer may include, for example, at least one of
BCP, Bphen, and BAlq, but is not limited thereto:
##STR00080##
A thickness of the hole blocking layer may be in a range of about
20 .ANG. to about 1,000 .ANG., for example, about 30 .ANG. to about
300 .ANG.. While not wishing to be bound by theory, it is
understood that when the thickness of the hole blocking layer is
within these ranges, the hole blocking layer may have improved hole
blocking ability without a substantial increase in driving
voltage.
The electron transport layer may further include at least one
selected from BOP, Bphen, Alq.sub.3, BAlq, TAZ, and NTAZ:
##STR00081##
In one or more embodiments, the electron transport layer may
include at least one of ET1 and ET2, but are not limited
thereto:
##STR00082##
A thickness of the electron transport layer may be in a range of
about 100 .ANG. to about 1,000 .ANG., for example, about 150 .ANG.
to about 500 .ANG.. While not wishing to be bound by theory, it is
understood that when the thickness of the electron transport layer
is within the range described above, the electron transport layer
may have satisfactory electron transport characteristics without a
substantial increase in driving voltage.
Also, the electron transport layer may further include, in addition
to the materials described above, a metal-containing material.
The metal-containing material may include a Li complex. The Li
complex may include, for example, Compound ET-D1 (lithium
quinolate, LiQ) or ET-D2:
##STR00083##
The electron transport region may include an electron injection
layer (EIL) that promotes flow of electrons from the second
electrode 19 thereinto.
The electron injection layer may include at least one selected
from, LiF, NaCl, CsF, Li.sub.2O, BaO, and LiQ.
A thickness of the electron injection layer may be in a range of
about 1 .ANG. to about 100 .ANG., for example, about 3 .ANG. to
about 90 .ANG.. While not wishing to be bound by theory, it is
understood that when the thickness of the electron injection layer
is within the ranges described above, the electron injection layer
may have satisfactory electron injection characteristics without a
substantial increase in driving voltage.
The second electrode 19 is disposed on the organic layer 15. The
second electrode 19 may be a cathode. A material for forming the
second electrode 19 may be selected from metal, an alloy, an
electrically conductive compound, and a combination thereof, which
have a relatively low work function. For example, lithium (Li),
magnesium (Mg), aluminum (Al), aluminum-lithium (Al--Li), calcium
(Ca), magnesium-indium (Mg--In), or magnesium-silver (Mg--Ag) may
be used as a material for forming the second electrode 19. In one
or more embodiments, to manufacture a top emission type
light-emitting device, a transmissive electrode formed using ITO or
IZO may be used as the second electrode 19.
Hereinbefore, the organic light-emitting device has been described
with reference to FIGURE, but is not limited thereto.
Another aspect of the present disclosure provides a diagnosis
composition including at least one organometallic compound
represented by Formula 1.
The organometallic compound represented by Formula 1 may provide
high luminescent efficiency. Accordingly, a diagnosis composition
including the organometallic compound may have high diagnosis
efficiency.
Such a diagnosis composition may be used in various applications
including diagnosis kits, diagnosis reagents, biosensors,
biomarkers, etc.
The term "C.sub.1-C.sub.60 alkyl group," as used herein, refers to
a linear or branched aliphatic saturated hydrocarbon monovalent
group having 1 to 60 carbon atoms, and examples thereof include a
methyl group, an ethyl group, a propyl group, an iso-butyl group, a
sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl
group, and a hexyl group. The term "C.sub.1-C.sub.60 alkylene
group," as used herein, refers to a divalent group having the same
structure as the C.sub.1-C.sub.60 alkyl group.
The term "C.sub.1-C.sub.60 alkoxy group," as used herein, refers to
a monovalent group represented by --OA.sub.101 (wherein A.sub.101
is the C.sub.1-C.sub.60 alkyl group), and non-limiting examples
thereof include a methoxy group, an ethoxy group, and an
iso-propyloxy (iso-propoxy) group.
The term "C.sub.2-C.sub.60 alkenyl group," as used herein, refers
to a hydrocarbon group formed by including at least one
carbon-carbon double bond in the middle or at the terminus of the
C.sub.2-C.sub.60 alkyl group, and examples thereof include an
ethenyl group, a propenyl group, and a butenyl group. The term
"C.sub.2-C.sub.60 alkenylene group," as used herein, refers to a
divalent group having the same structure as the C.sub.2-C.sub.60
alkenyl group.
The term "C.sub.2-C.sub.60 alkynyl group," as used herein, refers
to a hydrocarbon group formed by including at least one
carbon-carbon triple bond in the middle or at the terminus of the
C.sub.2-C.sub.60 alkyl group, and examples thereof include an
ethynyl group, and a propynyl group. The term "C.sub.2-C.sub.60
alkynylene group," as used herein, refers to a divalent group
having the same structure as the C.sub.2-C.sub.60 alkynyl
group.
The term "C.sub.3-C.sub.10 cycloalkyl group," as used herein,
refers to a monovalent saturated hydrocarbon monocyclic group
having 3 to 10 carbon atoms, and non-limiting examples thereof
include a cyclopropyl group, a cyclobutyl group, a cyclopentyl
group, a cyclohexyl group, and a cycloheptyl group. The term
"C.sub.3-C.sub.10 cycloalkylene group," as used herein, refers to a
divalent group having the same structure as the C.sub.3-C.sub.10
cycloalkyl group.
The term "C.sub.1-C.sub.10 heterocycloalkyl group," as used herein,
refers to a monovalent saturated monocyclic group having at least
one heteroatom selected from N, O, P, Si, and S as a ring-forming
atom and 1 to 10 carbon atoms, and non-limiting examples thereof
include a tetrahydrofuranyl group and a tetrahydrothiophenyl group.
The term "C.sub.1-C.sub.10 heterocycloalkylene group," as used
herein, refers to a divalent group having the same structure as the
C.sub.1-C.sub.10 heterocycloalkyl group.
The term "C.sub.3-C.sub.10 cycloalkenyl group," as used herein,
refers to a monovalent monocyclic group that has 3 to 10 carbon
atoms, at least one carbon-carbon double bond in the ring thereof,
and which is not aromatic in the entire molecular structure.
Non-limiting examples thereof include a cyclopentenyl group, a
cyclohexenyl group, and a cycloheptenyl group. The term
"C.sub.3-C.sub.10 cycloalkenylene group," as used herein, refers to
a divalent group having the same structure as the C.sub.3-C.sub.10
cycloalkenyl group.
The term "C.sub.1-C.sub.10 heterocycloalkenyl group," as used
herein, refers to a monovalent monocyclic group that has at least
one heteroatom selected from N, O, P, Si, and S as a ring-forming
atom, 1 to 10 carbon atoms, and at least one carbon-carbon double
bond in its ring. Non-limiting examples of the C.sub.1-C.sub.10
heterocycloalkenyl group include a 2,3-dihydrofuranyl group and a
2,3-dihydrothiophenyl group. The term "C.sub.1-C.sub.10
heterocycloalkenylene group," as used herein, refers to a divalent
group having the same structure as the C.sub.1-C.sub.10
heterocycloalkenyl group.
The term "C.sub.6-C.sub.60 aryl group," as used herein, refers to a
monovalent group having a carbocyclic aromatic system having 6 to
60 carbon atoms, and the term "C.sub.6-C.sub.60 arylene group," as
used herein, refers to a divalent group having a carbocyclic
aromatic system having 6 to 60 carbon atoms. Non-limiting examples
of the C.sub.6-C.sub.60 aryl group include a phenyl group, a
naphthyl group, an anthracenyl group, a phenanthrenyl group, a
pyrenyl group, and a chrysenyl group. When the C.sub.6-C.sub.60
aryl group and the C.sub.6-C.sub.60 arylene group each include two
or more rings, the rings may be fused to each other.
The term "C.sub.1-C.sub.60 heteroaryl group," as used herein,
refers to a monovalent group having a heterocyclic aromatic system
that has at least one heteroatom selected from N, O, P, Si, and S
as a ring-forming atom, and 1 to 60 carbon atoms. The term
"C.sub.1-C.sub.60 heteroarylene group," as used herein refers to a
divalent group having a heterocyclic aromatic system that has at
least one heteroatom selected from N, O, P, Si, and S as a
ring-forming atom, and 1 to 60 carbon atoms. Non-limiting examples
of the C.sub.1-C.sub.60 heteroaryl group include a pyridinyl group,
a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a
triazinyl group, a quinolinyl group, and an isoquinolinyl group.
When the C.sub.1-C.sub.60 heteroaryl group and the C.sub.1-C.sub.60
heteroarylene group each include two or more rings, the rings may
be fused to each other.
The term "C.sub.6-C.sub.60 aryloxy group, as used herein, indicates
--OA.sub.102 (wherein A.sub.102 is the C.sub.6-C.sub.60 aryl
group), and a C.sub.6-C.sub.60 arylthio group as used herein
indicates --SA.sub.103 (wherein A.sub.103 is the C.sub.6-C.sub.60
aryl group).
The term "monovalent non-aromatic condensed polycyclic group," as
used herein, refers to a monovalent group (for example, having 8 to
60 carbon atoms) that has two or more rings condensed to each
other, only carbon atoms as a ring-forming atom, and which is
non-aromatic in the entire molecular structure. Examples of the
monovalent non-aromatic condensed polycyclic group include a
fluorenyl group. The term "divalent non-aromatic condensed
polycyclic group," as used herein, refers to a divalent group
having the same structure as the monovalent non-aromatic condensed
polycyclic group.
The term "monovalent non-aromatic condensed heteropolycyclic
group," as used herein, refers to a monovalent group (for example,
having 2 to 60 carbon atoms) that has two or more rings condensed
to each other, has a heteroatom selected from N, O, P, Si, and S,
other than carbon atoms, as a ring-forming atom, and which is
non-aromatic in the entire molecular structure. Non-limiting
examples of the monovalent non-aromatic condensed heteropolycyclic
group include a carbazolyl group. The term "divalent non-aromatic
condensed heteropolycyclic group," as used herein, refers to a
divalent group having the same structure as the monovalent
non-aromatic condensed heteropolycyclic group.
The term "C.sub.5-C.sub.30 carbocyclic group," as used herein,
refers to a saturated or unsaturated cyclic group having 5 to 30
carbons as a ring-forming atom. Examples of the C.sub.5-C.sub.30
carbocyclic group include a monocyclic group and a polycyclic
group.
The term "C.sub.1-C.sub.30 heterocyclic group," as used herein,
refers to a saturated or unsaturated cyclic group having, at least
one heteroatom selected from N, O, P, Si, and S, other than 1 to 30
carbons, as a ring-forming atom. Examples of the C.sub.1-C.sub.30
heterocyclic group include a monocyclic group and a polycyclic
group.
At least one of substituents of the substituted C.sub.5-C.sub.30
carbocyclic group, substituted C.sub.2-C.sub.30 heterocyclic group,
the substituted C.sub.1-C.sub.60 alkyl group, the substituted
C.sub.2-C.sub.60 alkenyl group, the substituted C.sub.2-C.sub.60
alkynyl group, the substituted C.sub.1-C.sub.60 alkoxy group, the
substituted C.sub.3-C.sub.10 cycloalkyl group, the substituted
C.sub.1-C.sub.10 heterocycloalkyl group, the substituted
C.sub.3-C.sub.10 cycloalkenyl group, the substituted
C.sub.1-C.sub.10 heterocycloalkenyl group, the substituted
C.sub.6-C.sub.60 aryl group, the substituted C.sub.6-C.sub.60
aryloxy group, the substituted C.sub.6-C.sub.60 arylthio group, the
substituted C.sub.1-C.sub.60 heteroaryl group, the substituted
monovalent non-aromatic condensed polycyclic group, and the
substituted monovalent non-aromatic condensed heteropolycyclic
group may be selected from:
deuterium, --F, --Cl, --Br, --I, --CD.sub.3, --CD.sub.2H,
--CDH.sub.2, --CF.sub.3, --CF.sub.2H, --CFH.sub.2, a hydroxyl
group, a cyano group, a nitro group, an amino group, an amidino
group, a hydrazine group, a hydrazone group, a carboxylic acid
group or a salt thereof, a sulfonic acid group or a salt thereof, a
phosphoric acid group or a salt thereof, a C.sub.1-C.sub.60 alkyl
group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl
group, and a C.sub.1-C.sub.60 alkoxy group;
a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a
C.sub.2-C.sub.60 alkynyl group, and a C.sub.1-C.sub.60 alkoxy
group, each substituted with at least one selected from deuterium,
--F, --Cl, --Br, --I, --CD.sub.3, --CD.sub.2H, --CDH.sub.2,
--CF.sub.3, --CF.sub.2H, --CFH.sub.2, a hydroxyl group, a cyano
group, a nitro group, an amino group, an amidino group, a hydrazine
group, a hydrazone group, a carboxylic acid group or a salt
thereof, a sulfonic acid group or a salt thereof, a phosphoric acid
group or a salt thereof, a C.sub.3-C.sub.10 cycloalkyl group, a
C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10
cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl
group,
a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a
C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl
group, a monovalent non-aromatic condensed polycyclic group, a
monovalent non-aromatic condensed heteropolycyclic group,
--N(Q.sub.11)(Q.sub.12), --Si(Q.sub.13)(Q.sub.14)(Q.sub.15),
--B(Q.sub.16)(Q.sub.17), and --P(.dbd.O)(Q.sub.18)(Q.sub.19);
a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60
arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, and a monovalent
non-aromatic condensed heteropolycyclic group;
a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60
arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, and a monovalent
non-aromatic condensed heteropolycyclic group, each substituted
with at least one selected from deuterium, --F, --Br, --CD.sub.3,
--CD.sub.2H, --CDH.sub.2, --CF.sub.3, --CF.sub.2H, --CFH.sub.2, a
hydroxyl group, a cyano group, a nitro group, an amino group, an
amidino group, a hydrazine group, a hydrazone group, a carboxylic
acid group or a salt thereof, a sulfonic acid group or a salt
thereof, a phosphoric acid group or a salt thereof, a
C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a
C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a
C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60
arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, a monovalent non-aromatic
condensed heteropolycyclic group, --N(Q.sub.21)(Q.sub.22),
--Si(Q.sub.23)(Q.sub.24)(Q.sub.25), --B(Q.sub.26)(Q.sub.27), and
--P(.dbd.O)(Q.sub.28)(Q.sub.29); and
--N(Q.sub.31)(Q.sub.32), --Si(Q.sub.33)(Q.sub.34)(Q.sub.35),
--B(Q.sub.36)(Q.sub.37), and --P(.dbd.O)(Q.sub.38)(Q.sub.39),
wherein Q.sub.11 to Q.sub.19, Q.sub.21 to Q.sub.29, and Q.sub.31 to
Q.sub.39 may each independently be selected from hydrogen,
deuterium, --F, --Br, a hydroxyl group, a cyano group, a nitro
group, an amino group, an amidino group, a hydrazine group, a
hydrazone group, a carboxylic acid group or a salt thereof, a
sulfonic acid group or a salt thereof, a phosphoric acid group or a
salt thereof, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60
alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60
alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a
C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10
cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a
C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryl group
substituted with at least one selected from a C.sub.1-C.sub.60
alkyl group and a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60
aryloxy group, a C.sub.6-C.sub.60 arylthio group, a
C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic
condensed polycyclic group, and a monovalent non-aromatic condensed
heteropolycyclic group.
When a group containing a specified number of carbon atoms is
substituted with any of the groups listed in the preceding
paragraphs, the number of carbon atoms in the resulting
"substituted" group is defined as the sum of the carbon atoms
contained in the original (unsubstituted) group and the carbon
atoms (if any) contained in the substituent. For example, when the
term "substituted C.sub.1-C.sub.60 alkyl" refers to a
C.sub.1-C.sub.60 alkyl group substituted with C.sub.6-C.sub.60 aryl
group, the total number of carbon atoms in the resulting aryl
substituted alkyl group is C.sub.7-C.sub.120.
Hereinafter, a compound and an organic light-emitting device
according to embodiments are described in detail with reference to
Synthesis Example and Examples. However, the organic light-emitting
device is not limited thereto. The wording "B was used instead of
A" used in describing Synthesis Examples means that an amount of A
used was identical to an amount of B used, in terms of a molar
equivalent.
EXAMPLE
Synthesis Example 1: Synthesis of Compound 2
##STR00084## ##STR00085##
Synthesis of Intermediate 2-4
5 grams (g) (32.88 millimoles, mmol) of a (2-methoxyphenyl)boronic
acid, 8.5 g (29.31 mmol) of Intermediate 2-5, 10 g (73.27 mmol) of
K.sub.2CO.sub.3, and 1.7 g (1.46 mmol) Pd(PPh.sub.3).sub.4 were
mixed together with 190 milliliters (mL) of THF and 95 mL of
H.sub.2O, and the mixed solution was heated to a temperature of
80.degree. C. and was stirred under reflux for 16 hours. The
obtained reaction solution was cooled to room temperature and
extracted by using 400 mL of water and 400 mL of ethyl acetate to
obtain an organic layer. The organic layer was dried by using
MgSO.sub.4, and the residue obtained by evaporating the remaining
solvent was separated and purified by using silica gel column
chromatography to obtain 6.7 g (72%) of Intermediate 2-4. The
obtained compound was identified by LC-MS.
C.sub.17H.sub.19BrO: M.sup.+ 318.06
Synthesis of Intermediate 2-3
6.7 g (21.06 mmol) of Intermediate 2-4 and 8 g (31.59 mmol) of
bis(pinacolato)diboron, 3.1 g (31.58 mmol) of potassium acetate,
and 1 g (1.26 mmol) of Pd(PPh.sub.3).sub.2Cl.sub.2 were mixed
together with 100 mL of toluene, and the mixed solution was heated
to a temperature of 120.degree. C. and was stirred under reflux for
8 hours. The obtained reaction solution was cooled to room
temperature and extracted by using 300 mL of water and 300 mL of
ethyl acetate to obtain an organic layer. The organic layer was
dried by using MgSO.sub.4, and the residue obtained by evaporating
the remaining solvent was separated and purified by using silica
gel column chromatography to obtain 5.8 g (75%) of Intermediate
2-3. The obtained compound was identified by LC-MS.
C.sub.23H.sub.31BO.sub.3: M.sup.+ 366.24
Synthesis of Intermediate 2-2
5.8 g (15.8 mmol) of Intermediate 2-3, 8.3 g (17.4 mmol) of
Intermediate A
(2-chloro-6-(9-(pyridin-2-yl)-9H-fluoren-9-yl)pyridine), 5.5 g (40
mmol) of K.sub.2CO.sub.3, and 1.2 g (1 mmol) of Pd(PPh.sub.3).sub.4
were mixed together with 100 mL of THF and 50 mL of H.sub.2O, and
the mixed solution was heated to a temperature of 80.degree. C. and
was stirred under reflux for 16 hours. The obtained reaction
solution was cooled to room temperature and extracted by using 300
mL of water and 300 mL of ethyl acetate to obtain an organic layer.
The organic layer was dried by using MgSO.sub.4, and the residue
obtained by evaporating the remaining solvent was separated and
purified by using silica gel column chromatography to obtain 6 g
(68%) of Intermediate 2-2. The obtained compound was identified by
LC-MS.
C.sub.40H.sub.34N.sub.2O: M.sup.+ 558.27
Synthesis of Intermediate 2-1
6 g (10.75 mmol) of Intermediate 2-2 and 35 g (300 mmol) of
pyridine hydrochloride were placed into a sealed tube, and the
mixed solution was heated to a temperature of 180.degree. C. and
was stirred for 16 hours. The obtained reaction solution was cooled
to room temperature, and extracted by using a sodium bicarbonate
aqueous solution, methylene chloride (MC), and H.sub.2O to obtain
an organic layer. The organic layer was dried by using MgSO.sub.4,
and the residue obtained by evaporating the remaining solvent was
separated and purified by using silica gel column chromatography to
obtain 3.5 g (60%) of Intermediate 2-1. The obtained compound was
identified by LC-MS.
C.sub.39H.sub.32N.sub.2O: M.sup.+ 544.25
Synthesis of Compound 2
3.5 g (6.4 mmol) of Intermediate 2-1, 3.2 g (7.7 mmol) of potassium
tetrachloroplatinate, and 200 mL of an acetic acid were mixed
together with each other, and the mixed solution was heated to a
temperature of 120.degree. C. and was stirred under reflux for 16
hours. The obtained reaction solution was cooled to a room
temperature, and an extraction process was performed thereon by
using a sodium bicarbonate aqueous solution, water, and 300 mL of
ethyl acetate to obtain an organic layer. The organic layer was
dried by using MgSO.sub.4, and the residue obtained by evaporating
the remaining solvent was separated and purified by using silica
gel column chromatography to obtain 2.6 g (55%) of Compound 2. The
obtained compound was identified by LC-MS.
C.sub.39H.sub.30N.sub.2OPt: M.sup.+ 737.20
Synthesis Example 2: Synthesis of Compound 5
Compound 5 was synthesized in the same manner as in Synthesis
Example 1, except that 3,5-dibromo-1,1'-biphenyl was used instead
of Intermediate 2-5 in synthesizing Intermediate 2-4. The obtained
compound was identified by LC-MS.
C.sub.41H.sub.26N.sub.2OPt: M.sup.+ 757.17
Synthesis Example 3: Synthesis of Compound 8
Compound 8 was synthesized in the same manner as in Synthesis
Example 1, except that
3,5-dibromo-3',5'-di-tert-butyl-1,1'-biphenyl was used instead of
Intermediate 2-5 in synthesizing Intermediate 2-4. The obtained
compound was identified by LC-MS.
C.sub.49H.sub.42N.sub.2OPt: M.sup.+ 869.29
Synthesis Example 4: Synthesis of Compound 10
Compound 10 was synthesized in the same manner as in Synthesis
Example 1, except that a 5-tert-butyl-2-methoxyphenylboronic acid
and 1,3-dibromobenzene were used instead of a
(2-methoxyphenyl)boronic acid and Intermediate 2-5 in synthesizing
Intermediate 2-4. The obtained compound was identified by
LC-MS.
C.sub.39H.sub.30N.sub.2OPt: M.sup.+ 737.20
Synthesis Example 5: Synthesis of Compound 36
##STR00086## ##STR00087##
Synthesis of Intermediate 36-4
Intermediate 36-4 was synthesized in the same manner as in
Synthesis of Intermediate 2-4 in Synthesis Example 1, except that
Intermediate 36-5 was used instead of Intermediate 2-5.
Synthesis of Intermediate 36-3
Intermediate 36-3 was synthesized in the same manner as in
Synthesis of Intermediate 2-3 in Synthesis Example 1, except that
Intermediate 36-4 was used instead of Intermediate 2-4.
Synthesis of Intermediate 36-2
Intermediate 36-2 was synthesized in the same manner as in
Synthesis of Intermediate 2-2 in Synthesis Example 1, except that
Intermediate 36-3 and Intermediate B were used instead of
Intermediate 2-3 and Intermediate A.
Synthesis of Intermediate 36-1
Intermediate 36-1 was synthesized in the same manner as in
Synthesis of Intermediate 2-1 in Synthesis Example 1, except that
Intermediate 36-2 was used instead of Intermediate 2-2.
Synthesis of Compound 36
Compound 36 was synthesized in the same manner as in Synthesis of
Compound 2 in Synthesis Example 1, except that Intermediate 36-1
was used instead of Intermediate 2-1. The obtained compound was
identified by LC-MS.
C.sub.36H.sub.33N.sub.3OPt: M.sup.+ 718.23
Synthesis Example 6: Synthesis of Compound 44
##STR00088## ##STR00089## ##STR00090##
Synthesis of Intermediate 44-4
Intermediate 44-4 was synthesized in the same manner as in
Synthesis of Intermediate 2-4 in Synthesis Example 1, except that
Intermediate 44-5 was used instead of Intermediate 2-5.
Synthesis of Intermediate 44-3
Intermediate 44-3 was synthesized in the same manner as in
Synthesis of Intermediate 2-3 in Synthesis Example 1, except that
Intermediate 44-4 was used instead of Intermediate 2-4.
Synthesis of Intermediate 44-2
Intermediate 44-2 was synthesized in the same manner as in
Synthesis of Intermediate 2-2 in Synthesis Example 1, except that
Intermediate 44-3 and Intermediate C were used instead of
Intermediate 2-3 and Intermediate A.
Synthesis of Intermediate 44-1
Intermediate 44-1 was synthesized in the same manner as in
Synthesis of Intermediate 2-1 in Synthesis Example 1, except that
Intermediate 44-2 was used instead of Intermediate 2-2.
Synthesis of Compound 44
Compound 44 was synthesized in the same manner as in Synthesis of
Compound 2 in Synthesis Example 1, except that Intermediate 44-1
was used instead of Intermediate 2-1. The obtained compound was
identified by LC-MS.
C.sub.48H.sub.43N.sub.3OPt: M.sup.+ 872.31
Synthesis Example 7: Synthesis of Compound 66
##STR00091## ##STR00092##
Synthesis of Intermediate 66-2
Intermediate 66-2 was synthesized in the same manner as in
Synthesis of Intermediate 2-2 in Synthesis Example 1, except that
Intermediate D was used instead of Intermediate A.
Synthesis of Intermediate 66-1
Intermediate 66-1 was synthesized in the same manner as in
Synthesis of Intermediate 2-1 in Synthesis Example 1, except that
Intermediate 66-2 was used instead of Intermediate 2-2.
Synthesis of Compound 66
Compound 66 was synthesized in the same manner as in Synthesis of
Compound 2 in Synthesis Example 1, except that Intermediate 66-1
was used instead of Intermediate 2-1. The obtained compound was
identified by LC-MS.
C.sub.44H.sub.34N.sub.4OPt: M.sup.+ 829.24
Example 1
An ITO glass substrate, on which an ITO electrode (anode) was
deposited, was cut to a size of 50 millimeters (mm).times.50
mm.times.0.5 mm, ultrasonically cleaned using acetone iso-propyl
alcohol and pure water each for 15 minutes, and exposed to
irradiation of UV light for 30 minutes and ozone to clean.
Then, m-MTDATA was deposited on the ITO electrode (anode) at a
deposition rate of 1 Angstroms per second (.ANG./sec) to form a
hole injection layer having a thickness of 600 Angstroms (.ANG.),
and .alpha.-NPD was deposited on the hole injection layer at a
deposition rate of 1 .ANG./sec to form a hole transport layer
having a thickness of 250 .ANG..
Compound 2 (as a dopant) and CBP (as a host) were respectively
co-deposited on the hole transport layer at a deposition rate of
0.1 .ANG./sec and a deposition rate of 1 .ANG./sec to form an
emission layer having a thickness of 400 .ANG..
BAlq was deposited on the emission layer at a deposition rate of 1
.ANG./sec to form a hole blocking layer having a thickness of 50
.ANG., Alq.sub.3 was deposited on the hole blocking layer to form
an electron transport layer having a thickness of 300 .ANG., LiF
was deposited on the electron transport layer to form an electron
injection layer having a thickness of 10 .ANG., and then, Al was
vacuum-deposited on the electron injection layer to form a second
electrode (cathode) having a thickness of 1,200 .ANG., thereby
completing the manufacture of an organic light-emitting device
having a structure of ITO/m-MTDATA (600 .LAMBDA.)/.alpha.-NPD (250
.LAMBDA.)/CBP+Compound 2 (10%) (400 .ANG.))/BAlq (50
.LAMBDA.)/Alq.sub.3 (300 .ANG.)/LiF (10 .LAMBDA.)/Al (1,200
.ANG.).
Examples 2 to 5 and Comparative Examples 1 and 2
Organic light-emitting devices were manufactured in the same manner
as in Example 1, except that compounds shown in Table 2 were used
as a dopant, instead of Compound 2 in forming an emission
layer.
Evaluation Example 1: Evaluation on Characteristics of Organic
Light-Emitting Devices
The driving voltage, luminescence efficiency, power efficiency,
color purity, quantum efficiency, roll-off ratio, and lifespan
(T.sub.95) of the organic light-emitting devices manufactured in
Examples 1 to 5 and Comparative Examples 1 and 2 were evaluated.
Results thereof are shown in Table 2. A current-voltage meter
(Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used
as evaluation devices. The lifespan (T.sub.95) (at 6,000 nit) was
evaluated as a period of time taken until the luminance was reduced
to 95% of initial luminance. The roll-off ratio was calculated
using Equation 20: Roll-off ratio={1-(efficiency (at 9,000
nit)/maximum emission efficiency)}.times.100%. Equation 20
TABLE-US-00002 TABLE 2 Driving Luminescence Power Quantum Roll-off
Lifespan voltage Efficiency Efficiency Efficiency ratio (hr) Dopant
(V) (cd/A) (lm/W) CIEx CIEy (%) (%) (T.sub.95) Example 1 Compound 2
4.8 46.5 31.2 0.344 0.604 19 21 230 Example 2 Compound 8 4.9 47.1
31.0 0.342 0.604 19 20 245 Example 3 Compound 10 4.7 41.3 31.5
0.340 0.604 19 10 220 Example 4 Compound 36 5.0 43.1 34.0 0.344
0.604 19 18 185 Example 5 Compound 66 5.1 45.2 33.2 0.349 0.604 19
20 210 Comparative Compound A 5.2 40.2 30.1 0.344 0.604 18 22 180
Example 1 Comparative Compound B 6.5 35.2 20.4 0.352 0.604 18 32 50
Example 2
##STR00093## ##STR00094##
Based on Table 2 results, it was determined that the organic
light-emitting devices of Examples 1 to 5 had excellent driving
voltage, luminescence efficiency, power efficiency, color purity,
quantum efficiency, roll-off ratio, and lifespan characteristics,
compared to those of the organic light-emitting devices of
Comparative Examples 1 and 2.
The organometallic compound according to embodiments may have
excellent electric characteristics and thermal stability.
Accordingly, an organic light-emitting device including the
organometallic compound may have excellent driving voltage,
luminescence efficiency, power efficiency, color purity, and
lifespan characteristics. In addition, since the organometallic
compound has excellent phosphorescence characteristics, a diagnosis
composition having high diagnosis efficiency may be provided by
using the organometallic compound.
It should be understood that embodiments described herein should be
considered in a descriptive sense only and not for purposes of
limitation. Descriptions of features or aspects within each
embodiment should typically be considered as available for other
similar features or aspects in other embodiments.
While one or more embodiments have been described with reference to
the figures, it will be understood by those of ordinary skill in
the art that various changes in form and details may be made
therein without departing from the spirit and scope of the present
disclosure as defined by the following claims.
* * * * *